


Touch Me, Teacher

by lavenderlover



Category: Supernatural
Genre: BDSM, Body Positivity, Come Kink, DDLG, Daddy Kink, Daddy dom little girl, Dean Winchester masturbating, Domspace, Exhibitionism, F/M, Fucking, Kinky, Lemon, Little Space, Lust, M/M, Masturbation, Multi, Other, Professor Kink, Sex, Smut, Spying, Subspace, Vibrators, cgl, cumkink, dean winchester wanking, exhibition, female masturbation also, i feel you girl, i'd be distracted if dean was my teacher too, naughty reader, pantysniffing, probably the hottest samxdeanxreader fanfic about, scatterbrained reader at times, teacher/student relationship, there's something in it for everyone, too much lust really, various states of professional and unprofessional undress, voyerism
Language: English
Status: In-Progress
Published: 2017-03-26
Updated: 2018-10-03
Packaged: 2018-10-10 23:10:34
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 17
Words: 30,055
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10449663
Author URL: https://archiveofourown.org/users/lavenderlover/pseuds/lavenderlover
Summary: In which Dean Winchester is your drama Professor and you're an adorable and seductive young student.One day, after a particularly frustrating class, Professor Winchester asks to see you after school. When you oblige him, you are surprised to find him hunched over his desk, masturbating in assumed solitude. Things just get crazier (and sexier) from there.Get swept up in a whirlwind of dramas, from misplaced bags to vibrating dildos, threesomes with the Winchesters, innuendos with the gorgeous Castiel, and the internal turmoil that follows an older man harboring a secret affection for one of his brightest students. There's passion, there's embarrassment, there's unspeakable lust, and best of all: there're shameless indulgences.





	1. The Drama Begins

**Author's Note:**

> This is my first time posting a story on one of my favourite fan-fiction sites! I'm super excited to be sharing this with you guys. Hopefully y'all like it; if you do, make sure to leave some love (it truly makes my day). Also leave suggestions! I've got a pretty clear plan of what I want to happen in this story, but there's nothing more powerful than audience persuasions.
> 
> Thanks, lovelies, let's get to the story! If you have the Y/N Plugin, it should change all instances of "Y/N" to your actual name, which is awesome! Get it here: http://interactivefics.tumblr.com

You're sitting in class, pen in hand, and trying not to stare at Professor Winchester and his _goddamned delicious ass_ when he turns around from the board and smiles at you, making your heart flutter. You've had an uncontrollable crush on him ever since you can remember, pretty much from the moment you met him actually. It's girly and it's silly but you couldn’t shake those feelings, so you do what you can to push the all-consuming erotic thoughts out of your head.

You often have no luck.

"You look like you have something to say, Miss Y/N." He tilts his head as he caps the lid of his whiteboard marker, his posture going relaxed. "Hopefully it's something drama-related and not you daydreaming in the clouds again?" His teasing makes you swoon even more, and you squeeze out a smile that you hope isn't too dorky.

"Oh, I was just wondering, when will we be performing our monologues?" You manage to ask, coming up with something coherent so you don't look like a giant goofball. “How many minutes do we need by the end of the week?”

He nods at you while you speak to him, like he’s listening to your deepest desires, and it makes your voice waver. You ignore it. His deep green eyes are doing some terrible, wonderful things to you, and it’s only intensified when he speaks. “Excellent question. We will be presenting in a fortnight from now. I expect you all to have three minutes by Friday.”

The class grumbles at the impending workload, but you grin. You’d been working on your piece for quite some time now, rehearsing and practising your lines in any spare time you got. Surely not just to please Professor Winchester, right? Of course. You're just a very conscientious student. Grades are important, and so is Professor Winchester’s approval… damn it! So maybe it is a little bit about him.

You and your classmates get time to work on your performances, and you’re glad you get to stretch your bones. Drama is fun. It’s one of those classes where you can be silly and free, and move around at the same time. Sitting for too long just makes you restless — but then again, so does your aforementioned drama teacher.

“Y/N!” You hear from across the room, which makes you stop daydreaming. “I don’t see you working!” His voice is like melted chocolate and electric sex, and really, it drives you wild. When he looks at you with those eyes… your lust is almost palpable. “Come and show me what you have so far in five, okay?”

“Okay, sir!” You call back, and try working without being distracted. You get out a few lines, but it’s not as much as you’d like to do. Monologues are the worst, because it always feels strange, practicing to yourself. Sure, you’ve gotten used to it, but it always leaves you a little less confident than a group performance. It's all all on you.

When the teacher of your dreams finishes with another student, he calls you to his modest desk and asks you to perform your piece.

“It’s not much,” you say timidly, wringing your hands together. _Damn, why does he make you so nervous?_   “But I hope you like it. Ahem.” You step back, getting into place. “Ah gentle bird, let your wings unfurl and carry me to the skies! I know not what awaits me there, but I hope it be sweet.” You pause, breaking out of character. “Sorry, I know it’s short. There’s more but it’s kind of all jumbled at the moment and—”

"Hey, Y/N, it’s fine. Good work so far, kid. But you ought to know that you are a little bit behind everyone else. Are you struggling?” The way he looks so concerned makes you weak at the knees — his eyebrows furrow, like he’s poring over a drama thesis, and those sinful lips part just the slightest, like a silent invitation. Your breath catches before you can speak.

You can’t help but notice that you’re slowly falling apart in front of him, and that beautiful gaze is making you nervous. “Oh, fuck,” you accidentally say out loud, and his eyes widen. He doesn’t press on it, which you’re thankful for, but it’s probably because you start talking again so quickly he doesn’t have room to interrupt. “No, yeah, I understand. I understand. I’m behind because I’m working on the backstory. I swear I’ve gotten it written down, just haven’t memorised it yet. Three minutes by Friday for sure.”

He chuckles, shaking his head ever so slightly. You see him shift that beautiful body of his in his chair, leaning forward to rest his elbows on the desk. You stare at his arms — the flesh exposed as he has rolled up his button-down shirt. Underneath your clothes, you’re starting to feel a little too hot. “Y/N, why do you always seem so nervous around me? Think of me as your friend, like you know me out of school.”

“If I knew you out of school sir, we definitely wouldn’t just be friends,” you say without thinking, and then you immediately clap a hand to your mouth. Where on earth is your head today? All kinds of words are spilling from your lips! Professor Winchester stiffens, his jaw falling open, but then he quickly composes himself, laughing it off. You’re beyond mortified. You can’t even apologize.

Standing up and brushing off his well-fitting trousers, he gives you a very stern look. “I must remind you that I’m the person in charge of you while you’re in my class, and thus, you’re in my hands. To abuse my power and say something to encourage more comments like _that_ wouldn’t be very orthodox, would it?” You nod solemnly. His tone is reprimanding and you know that, you understand that what you said was wrong and embarrassing. But when he leaves to help someone else and _winks_ at you before turning his back completely, you’re left in a puddle of arousal. This man is wearing you down and he doesn't even know it. Or maybe he does. You don't know what's worse.

“Jesus, I’m going to have to buy some new batteries after tonight…” you mumble to yourself, slouching your body. You perk straight back up when you see your professor turn his attention back towards you, as if remembering something.

“Oh! And by the way, Y/N, I’d like to see you after school. I hope that’s all right. There’re some things I'd like to discuss.”

“Great!” You say in a voice too chipper, just as the bell goes, and clutch your books hard to your chest as you all but run out of the room. _Great_ , you think sarcastically. Just great.

**Notes for the Chapter:**

> And there we have it, folks! The first chapter. The actual masturbation comes in the next one, so make sure to stay tuned! It's a hot one. Oh, Professor, why don't you just touch us? It's an eternal struggle. Anyway, thanks for reading, looking forward to having you back soon!


	2. Professor Orgasm

**Summary for the Chapter:**

> Professor Winchester. Masturbating. Cussing. Coming. What more is there to want?

**Notes for the Chapter:**

> I loved writing this. When I mentioned shameless indulgences in the story summary, I just hope you all know I wasn't kidding. Masturbation is so often underrated, imo. Like all the sexytimes are awesome and arousing and stimulating but when you read just a really good, dirty, depraved self-pleasure scene... it just does stuff to me. 
> 
> I hope you all get your rocks off to this, you dirty things.

The end of the day couldn't come any sooner. All your other classes had gone by slower that what seemed possible, and your anxiety is growing by the minute. What does the Professor want to speak to you about? Are you failing? Is he going to kick you out of the class? Is he going to profess his undying love for you? You giggle at the last part, shaking your head. _Yeah, right._

You step up to the drama hall, bag slung over your back, hair all in a flurry. Honestly, you look like a hot mess, but it doesn't matter. Your hand is hovering over the door when you hear footsteps. So he's there. _Of course, why wouldn't he be?_   The reality of your situation is starting to dawn on you. This isn't some fairytale, a fun play with a happy ending. Your actions have consequences, and this is the result. You're probably failing, failing, _failing!_ Shakily you gather your wits and knock, breathing in and out. No response. You knock once more. No response again.

So, what, is he ignoring you now? You walk in anyway, looking around the bare hall. There’s nothing but wooden floors and black curtains.

"Professor Winchester?" You call out, confused, having heard him on the other side of the door not a moment ago. "I'm here—you… you called me here, before? Sir?"

 _Are you just imagining the noises?_   You _are_ in a state of distress, after all, could you be hearing things? You're starting to become unsure of yourself when you walk up to his office and see his perfectly designed body hunched over some paperwork. You're about to walk in when you notice something… odd.

Oh.

_Oh._

His office is a lot nicer than the rickety desk and chair he uses out in the hall. His work is piled high on the lavish wooden table, the lamp on his left illuminating his face from behind like an angel. He hasn't seen you yet, since he's a little busy, but oh boy, _you can see him._

You don't even know if your brain has the mental capacity to understand what's unfolding before you. Your teacher, your _professor,_ has his perfectly-fitted trousers around his ankles, belt forgotten on the floor, with a fist around his cock. _He's masturbating in his office!_ And you're _watching_ him!

Your mind goes into overdrive, wondering how you should react. He's masturbating in his office, _at school,_ with the door open. Jesus Christ. As his hand glides over his dick, his left arm is clenching the desk, as if the pleasure is too intense to bear. His hunch loosens, legs falling even more open, and you see his balls under the light of the lamp. The tight hole that his fingers create furiously moves over the head, the shaft, to then bounce off the pillowy-ballsack and start all over again. You've never seen him look so depraved before. You've never seen _anyone_ look so depraved before.

He moans to himself quietly, trying to save that last shred of modesty. The sweat is rolling off his forehead, in tiny droplets of rain that make trails down his neck. You're fixated on them, wanting to know how they'd taste. Your panties are wet, your breathing is shallow, your cheeks are red and you're not even the one touching yourself.

Professor Winchester's legs start to spasm, the muscle just underneath the skin moving visibly. His legs quake, his laboured breaths get even more ragged, and you know what's about to happen but you don't believe it. You start to feel bad for spying, you're even about to turn yourself away when he does something you don't expect. As his head pulses with the desire to come, he haphazardly pulls up the bottom of his button-up with his left hand, exposing his lower stomach and bellybutton.

His abs are to die for, you conclude, and then go a bright red when you take a look at his pubic hair. He's trimmed. _Why does that make you feel so turned on?_ You expected no less, he's a tidy man, and with that trimmed beard, why not that too? You're not sure how you haven't passed out from embarrassment yet.

He throws his head back, his hand stroking erratically now, balls rising to meet the base of his dick. Struggling to pull his shirt up any higher, he decides it's not worth it, and moans so loud you gasp audibly.

"Fuck!" He groans through gritted teeth. And then he's coming, he's really _coming,_ your hot professor is orgasming all over his lower stomach and his dick is pulsing with each spurt of it. You can't believe what's happening, and you tremble with lust and adrenaline and confusion as you watch your teacher come completely undone.

His hand pumps even after his cock stops shooting come, riding out the orgasm until his head is used and glossy, a deep red colour. There's come all over his hands and dick, and not to mention his stomach. His body slumps backwards as he sighs contentedly. The smile on his face is so wide and happy for a second you forget what just happened.

There's a moment of bliss, and then the Professor seems to realise where he is. He looks around and you duck behind the side of the door, scurrying off to the entrance of the building. You fix your hair, straighten your clothes, and ignore the arousal that's just about dripping through your clothes. You wait a few moments, giving him time to clean everything up, and start slowly walking back to his office, making sure to be as loud as possible.

"Professor Winchester?" You call, your voice echoing off the walls. You can tell he's heard you this time, because there's a faint curse and then a sound of a man scrambling to clean up the come from his body. Your gentle feet grace the floor slowly, eyes wide and doe-like. Something inside you has changed forever, and you have no idea how you're about to face the man you'd just witnessed orgasm. 

**Notes for the Chapter:**

> Remember to leave something special down below if you wanna read more of a particular kink/thing/scene! Reading your comments breaks me into the biggest smile, I swear. It's lovely chatting with you all!


	3. Studential Confessions

**Summary for the Chapter:**

> You accidentally let something slip that you probably should've have. Things escalate. Professor Winchester has never been more embarrassed in his entire life.

**Notes for the Chapter:**

> Have I mentioned I love getting characters into awkward situations?

You're approaching the office again when he appears from the doorframe, giving you his regular thousand-watt smile. And yet, something doesn't seem right this time. You know something so deep and intimate about him, and he hasn't the slightest clue. You notice how he doesn't go for a handshake and you chuckle to yourself.

"What's so funny, Y/N?" He asks in a playful manner, looking a lot more composed than a person who'd just come their brains out should. He re-adjusts his shirt and your eyes wander down against your better judgement. _Just a moment ago,_ you think, _he was half-naked in his office._ When you don’t answer him, his smile falls. "Y/N? What's wrong? You look like you've just seen a ghost."

_Not quite._

You cough, blinking a few times before managing to say anything. It's incredibly hard to talk to him while looking him in the eyes. Fuck. "It's nothing, sir. If I may ask, why did you bring me here? I'm not… _failing_ , am I?"

"What? No, no, not at all! Is that what you were thinking? Oh, no, Y/N. Take a seat." He sits down on one of the bleachers inside the hall, and you sit beside him, turning your body to face him fully. When you're this close you can smell his cologne. And his sweat, too. It's oddly attractive. "I've just noticed that you've been a little distracted in class, which isn't like you. Your work is always exemplar, we both know that." You smile and dip your head at his praise. "But it looks like something is bothering you. Is everything okay at home? Is everything okay at school? If you're being bullied I can—"

Your brows jump, eyes going wide. "No! I'm not being bullied or anything. Really, I'm fine." How are you supposed to tell him that you've just been staring at his ass all day in class and that's why you've been paying less attention to the actual work? You scramble for any excuse to placate him, but you can't think of the one that sounds the most believable, so you use them all. "Tired, exams, uh, stress… yeah. I'll be back on track before you know it, sorry for slacking off the past week. I'll do better. I promise."

His dark green irises are softening at your words, and you're glad he believes you. You suppose that your less-than-ethical crush is safe for now. The two of you are so close and it's driving you crazy. You look at his face, at the freckles that span over his nose and cheeks, at those lips that you _know_ are capable of amazing things, at the smile that's so genuine it hurts. You just want to jump his bones! Or, rather, one figurative bone in particular…

"…feeling like you've been a little more disconnected lately, which is unusual because I thought drama was one of your favourite subjects, well— not that you've ever said that, I guess I kind of just assumed, ah—Y/N, are you even listening?"

"Hm? Yes, of course, sir."

He stares at you blankly.

"Y/N."

"Sir."

"If there's something that's bothering you, I'd like you to tell me." He puts a hand on your shoulder, and its warm and comforting and then you do the unthinkable.

"I saw you masturbating."

"And whatever it is, I'm sure we’ll be able to figure it out— _what did you just say?_ " He grips your shoulder tight, mouth falling open. You squirm out of his grasp, hands completely covering your reddening face. You want to fall into the earth and die. "Y/N, what did you say? Why would you say that you—"

"I, I, I saw you," you squeak out, moving even further backwards. You're about two meters away from him now, cowering in embarrassment. "I was here earlier, I— I went wandering, and I saw you, in your office — I'm so sorry! I should have just left!"

He's looking at you incredulously, a mix of seething and humiliated. "You _watched_ me? Do you even understand how completely wrong and immoral that is?!" He's yelling now, jaw hard and muscles tight, standing up to pace around the room. You're nearly in tears.

"You were the one masturbating on school grounds!" You shoot back, and then everything goes silent. He stops pacing, stops yelling, and turns to look at you. You don't know what he's about to do next, but you have one hand on the pepper spray in your bag. Just in case, of course. You're a smart woman.

He doesn't move towards you, though. Just sighs and sits down on the floor, hanging his head. "How long." His voice is broken.

You pause, your face finally uncovered fully. "How long what?"

"How long where you watching me, uh… you know."

"I don't know!" You shriek, throwing your bag at him, which he catches without a second thought, "a few seconds? Five minutes? Ten minutes?! Time just seemed to fly by!"

He holds his face in both hands. "Oh my God," he says. When he takes a few deep breaths, he stands back up, and characteristically brushes off his trousers. Your eyes follow his hands. He collects himself. He breathes. You watch. "Listen. I'm wrong in this situation. It was a momentary lapse in character I assure you, and I had no intention of anyone coming in to see, it wasn't some sort of kinky joyride or anything, I'd _never_ put my students into a situation like that."

You stare at him and he avoids your gaze. "You asked me to see you after school," you say, voice more confident than you felt, "and then you start masturbating. What the fuck? Couldn't you wait until after?!"

"Language," he warns, and a fire ignites in your eyes.

"Don't fucking lecture me about my language when I just saw you getting your rocks off in your office," you spit, turning away from him.

His demeanour changes completely. "Okay, okay, Y/N, I'm sorry." He takes a few steps towards you in quick succession. "Don't be angry, don't be angry. You're not going to… report me, are you?" After a tense pause, he says something that makes you nearly fall to your knees. "Because, God, you've got to understand — you've now got the power to fucking _ruin_ me."


	4. Momentary Lapse in Character

**Summary for the Chapter:**

> You and the Prof have a slightly more heated conversation, in which vices are revealed. You find strength inside yourself and leave him in a bit of a stupor. And what will you do? Will you ruin him? We'll see.

**Notes for the Chapter:**

> Don't worry, smut coming soon. Guess this fic does classify as a slow-burn... ;D

You bite your lip, eyes downcast. When he swears you feel yourself shudder, your body naturally falling closer to his. He plants both hands on your shoulders when it looks like you're going to double over. The two of you take a seat. "I couldn't report you, sir," you reply, voice uncertain of where it wants to go. Should you be confident? Timid? Ashamed? "But I just don't… get it. Is this a regular thing for you?"

 _Is it out of line to ask something like that?_ You shake the thought out of your head. If there's a line, you two have already flown past it. "No! God, no. I told you, momentary lapse in character." He licks his lips but it's not in a lustful way: he's nervous. "Listen, Y/N, I'm about get serious with you. I've been stressed out lately and today all my pent-up frustration seemed to meet its tipping point. Honestly, the last class I had, I was barely managing to keep it together. Everyone kept asking me why I was so cranky."

You laugh softly, your hand coming out of your pocket to hold your chin up. Your elbow digs in to your knee, but you don't care. "That's crazy," you say, teasing. You're surprised you have the confidence to sound anything but shaken up. "How old are you, fifteen? Horndog."

"Hey!" He raises his voice a little. "I may have done something completely out of line, but I'm still your teacher. I don't want our relationship to change because of this. And I'm in no position to be making demands, but I know you, Y/N. You're intelligent and empathic. I don't think you'd be so heartless as to destroy my entire decade-long teaching career." He speaks his words like he almost doesn't believe it, and he's just trying to be hopeful. But he's right. You could never do that to a person — and especially not _him._

He doesn't have to know that so soon, though. "Hm, we'll see," you say. "You have to tell me, though, what on Earth made you so frustrated you couldn't wait until you got home to get yourself off? Must have been pretty hot." You're still talking to him casually, even after his warning; because really, _he didn't want your relationship to change?_ As if that's even possible. You'd just seen him orgasm.

He sighs and rubs his temples, looking pained. You start to feel sorry for him, but you don't say anything. "No, I'm sorry. I can't do this."

"You know I have the administrators of this school on speed dial…" you blackmail, even though you're lying through your teeth.

Professor Winchester raises his eyebrows at your threat and throws his head back in exasperation, but there's a slight smile gracing his lips. "You serious? That's a dirty card to play, Y/N." When you don't reply, he continues. "It's not like you're going to believe me anyway." Still and as silent as ever, you manage to crack him. "Fine! It was… a student."

"Sir, you get more and more messed up the deeper we delve into your personality." It's said with a cool air of detachment, but inside your heart is racing. You know it can't be what you think, but the possibility alone causes your head to spin. You wonder how far you can push your luck. "Of course you know what my next question's going to be."

"I can't tell you who it is. I just can't. That's too far," he pleads, and it's  _almost_ pained enough to make you second-guess yourself. Almost.

You start to bring out your phone, slowly. He sees this and stands up, hands flying about, voice straining.

"Okay! Fuck, it was you! It was you the whole time, I was thinking about _you,_ I was thinking about fucking _you_ and tasting _you_ and taking _you!_ "

A silence rolls into the room and stays. He is still walking about the room, but when he realises he's said too much he falters. Every system in your body shuts down at his confession. You stare straight ahead of you— ignoring him, ignoring the arousal in your body, ignoring everything. You shake your head slowly and softly to yourself; you don't really know why.

"I see," you say in a monotonous tone, standing up and grabbing your things. You pick up your bag that your professor had left on the ground after you threw it at him. Your things clang around inside it as you put it on. "Well, if that will be all..." you still aren't looking at him; your movements are almost robotic. "I shall be going." You're pretty sure you're about to miss your bus, and since your parents are out on vacation, you don't feel much like walking. However, all the feelings that are swirling around in your head give you the fire that you need.  

You walk away without so much as a second glance, leaving the Professor with his shoulders stooped, arms lowered and palms facing you in a  _what just happened?_ gesture. "Wait, Y/N, please," he calls, but you don't acknowledge him. You walk. "It was our class today. Your body, the way you moved, your sweet voice, the way you _swear,_ your adorable attitude!" Your pace slows. "Your comments… _'if I knew you out of school, we wouldn't just be friends'_. Do you know how hard you made me when you said that? I had to excuse myself almost immediately. Please don't go just yet. Let's work this out. Let me give you a ride home."

At that, you finally face him, with your hand on the doorknob. Your face is so flushed it feels like it's sizzling. "Okay," you say shakily, "grab your keys."


	5. Misplacement

**Summary for the Chapter:**

> The Prof says some things that kind of break your heart, and after getting home you decide to call one of your best friends.

**Notes for the Chapter:**

> It's been a while, lovelies! The summer holidays have ended so my updates might be a little less frequent. Still writing, though, and hope to have a chapter out every fortnight or so!

In the front seat of Professor Winchester's car, your knees knock together nervously. The air is tense. Some pop song plays softly in the background, but it's not enough to ease the awkwardness. _Somebody has to say something,_ you think, _or I just might die of mortification._

He seems to read your mind. "So… I'd just like to take this time to apologize for being—actually, I'll just go ahead and apologize for everything that's happened within the past hour. All of it." His tone is so sincere and defeated, you can't help but feel sorry for him. You look over at him, at his face, as he stares straight ahead at the empty road. His hands clutch the wheel. You have a flashback to when his hands were clutching _something_ _else_ …

"Um!" You say quickly, to which he quirks an eyebrow. "It's okay. It's really—it's okay. It's—"

"—if you say _it's okay_ once more," he warns, and the two of you both laugh together. Your knees stop jittering, and his tone becomes more serious. "Y/N, I'd just like you to know that that  _incident_ was really out of line. And what—what I told you before, I hope… you keep that between us. I shouldn't have said that. I didn't mean it. I just— got carried away in the heat of the moment, and I wasn't thinking clearly. I hope you understand. I'm your teacher— I couldn't— I'm not allowed to..." his voice never reaches a point of comfortable conclusion, it just fades and fades until it's gone. "Yeah."

Your heart drops at his words. You can't think of a way to speak without sounding like you're about to cry, so you just hum as a response. For the rest of the ride home, you look out the window and press yourself against the door.

You can’t help but feel stupid. Of course, of course, of course he didn’t mean he was thinking about you in his most depraved private moments— he was probably just saying anything for you to not report him, even if it meant seducing you, one of his love-sick students. All he had to do was say some pretty words with that pretty mouth and you were gone; falling, melting like putty in his stupidly capable hands. You’d been naïve — taken advantage of, really — and now here you are trying to blend into the walls of his stupidly nice-smelling car.

When the wheels screech against your driveway, you get out of the car and nod, silently thanking him. He looks utterly distraught, eyes pleading, cheeks still flushed with embarrassment. He looks like he's expecting you to say something. _Well, too bad for him,_ you think, and your heart still stings at his earlier words. You make your way to the backyard door, hands clenched.

"Wait, Y/N! I just wanted to tell you that—" He calls, and you contemplate ignoring him. The next time he talks it looks as if he’d just changed his mind on what to say. "Where are you going?"

You don't bother turning around to answer. "My bedroom's 'round the back. Bye, sir."

You breathe out a sigh of relief when you hear the engine of his car roar to life. And just like that — as quickly as your professor had been tangled into your personal life— he was gone.

Naturally, the first thing you do when you flop onto your bed is call your best friend, Castiel. 

 

*

 

"I find it very hard to believe," comes a deep-sounding voice from the other end of the line, "that you received a ride from the teacher you've been lusting for your whole life and you didn't make a move."

You laugh, tying your hair back as you sat cross-legged on your bed. Your phone lay next to you, on speaker, as you did odd-jobs around your room. You'd just told Castiel about everything… well, minus the whole 'professor Winchester masturbating in his office' part. You omitted that, mostly to spare your own embarrassment, but also because you wanted to push that thought away as much as you could. The memory of how he'd rejected you so hard in the car is enough to make you wince.

"It's true!" You exclaim, laughing. It's a nice summer's evening, so the curtains are drawn back fully, and the windows are open to let in the breeze. "It was… really awkward. actually. Oh, but he's so handsome, Cas…"  _and heartbreaking,_ you think to yourself.

"So you keep saying…" he grumbles, and you can just imagine the lovably disgruntled expression on his face.

You'd been so excited to call him that you are still in your uniform. "The things I would do to that man, you have no idea. Yummy yummy!"

You hear the scratch of a pencil on the other end of the line. Castiel, the ever-industrious student, is most likely doing his homework — something that you should probably get to doing yourself. "Well, I have some idea," he teases, voice like silk, and you roll your eyes. "Since he's all I've been hearing about for the past year."

"Yeah, yeah," you say, and then quickly change the subject, ignoring the pang in your chest. "You doing Math or English?"

"Geography, actually," he replies. "Who would've thought the topography of Ancient Egypt could be so interesting?"

"You're my sweet little nerd, you know that, Cas?" At that, he laughs heartily, which causes a warm feeling to wrap around your heart. You're already starting to forget about Professor Winchester. Well… almost. Sighing, you lay back on your bed. "When you're done with that, could you help me with that Calculus 2 sheet? There were a few questions I couldn't crack for the life of me."

"Of course. Just give me a moment, I'm almost finished."

"Perfect, I need to change out of these clothes anyway. Be right back!" You leave your phone on the bed as you stand up, opening your closet door. _Pyjamas or casual clothes?_ You hum to yourself in thought, but in the back of your head, you know that pyjamas are the only way to go. Peeling off your dress, you throw it into the hamper, letting the summer breeze soothe your body. You hadn't realised how stressed out you'd been — your muscles are tense, slightly showing through the skin. You massage out the knots in your shoulders and focus on your breathing.

You look at yourself in the mirror. Your hair — as expected — is awry, windblown and framing your face. Your eyes are big and dewy, the colours fierce. Your body… you blush as you look at yourself, at the cute bra and matching panties that had little ribbons; you gaze at the smooth expanse of your skin, the curves of your figure. Grinning a little, you twirl around. Kisses are sent to the mirror. You are one devilish bastard.

From your bed, you hear Cas call. "I'm done! Are you okay over there?"

Startled, you jump back on your bed in your underwear. "Yep, sorry! Just got a little carried away." You laugh sheepishly. "Hang on a minute, I just need to get out my binder…"

Reaching to the side of your bed, your hand finds nothing but air. You wave your arm a little. You grunt. You always just tossed your bag to the side of your bed when you got home, but this time you must have misplaced it.

"Have you got your things?" You keep forgetting Castiel is still there. You promise to yourself that you will be a better best friend from now on. You jump up, pacing around, looking under pillows and piles of clothes.

"I can't find my bag!" You cry. Then, the realization dawns on you so hard that you all but faint onto your bed. "Oh, my God," you start, hands cupping your face, "I think— Cas, I think I left my bag in Professor Winchester's car! I was so nervous I just left without it…" In the distance, you hear your cat, _Rags_ , fumbling around in the back-yard. Perhaps he had he taken it, somehow?

There is a moment of dead air between you, and you feel your world spiralling down the drain. It feels like your whole life was falling apart, crumbling into your hands. You're starting to freak out when Cas — always the level-headed one — reassures you with his rich voice. "Don't worry, he's a very genuine person. I'm sure he'll keep it safe for you until whenever you can see him next."

Your skin breaks out in goosebumps. It occurs to you at once that you're still in your panties and bra, all the commotion having distracted you. "Yeah… you're probably right. I dunno, Cas, I'll talk to you later. I gotta get my head around all this, and I'm pretty sure a date with my vibrator is due."

He huffs. "No thanks to Professor Winchester, I assume. Okay, Y/N, I'll talk to you soon. Oh, and do try and catch up on all your homework."

_Beep._

Then Cas is gone and you're left with your own thoughts. As you run your fingers through your hair, you have the sudden urge to shout. _Nothing seems to be going right!_ And no matter how hard you try, you just can't seem to snap out of this nightmare.

"Could this day get any worse?!" You lament, burying your face deep into your pillow. Your legs kick at your bed, and then you slowly sit back up, defeated. "My hot professor is ruining my life!"

"Why, I'm sorry to hear that…"

"Mr Winchester?!"

**Notes for the Chapter:**

> Thanks to those of you who have been leaving sweet comments and encouragement. You all inspire me to continue with these wicked shenanigans!


	6. Tangled up in the Rosebushes

**Summary for the Chapter:**

> Oh, you darling thing, will you ever catch a break? 
> 
> Introducing: Murphy's Law, which states that anything that can go wrong, will go wrong.

**Notes for the Chapter:**

> Thanks to the cheeky little things that have been leaving such nice messages! I truly appreciate every single one of them! And please feel welcome to suggest things you want to see happen - I just might include it in the story!

You'd recognize that voice anywhere. You squeak, turning your body to see him at light speed and then realising you are half naked on your bed. Your hands go up to cover your bra, and then you swap to covering your panties, and then finally you opt for one arm to cover both sensitive areas. "What are you doing here?!"

He stares at you with his mouth agape, your bag hanging off his finger and resting on his back. In a flurry his eyes travel up and down your body, as if forgetting who you are, as if forgetting who _he is_. In a flash his whole face is red and he uses his free hand to physically shut his eyes. It's like he can't bear to close his eyes without forcing himself. " _Oh_ , fucking _shit_ , I didn't know that you were—"

"Gosh!" You shriek as you dive beneath the covers. "My God. Goodness! It's fine _I'munderthecoversnow_." You don't think you've ever been more embarrassed. Slowly, as if he doesn't believe you, he lowers his hand, and his eyes peek open. He can only see the colour of your bra straps and the smooth, silky expanse of your shoulders, but even that is too much for him. He keeps his eyes trained on your face in a cool, collected manner, but there's something simmering just beneath the surface of that facade.

He drops your bag to the floor. "Y/N, I'm so incredibly sorry…" he begins. It's obvious that he's at a loss for words, and honestly, you don't blame him. "I noticed once I was ten minutes from your house that you left your bag in the passenger's seat, and I thought I would return it, since it wasn't any type of inconvenience to me, and, well, erm…" there are simply no words. "I shouldn't have just walked in— I should have, well, I… should have knocked."

Your voice is meek. It comes out in a volume just slightly above a whisper. "Thank you for bringing my bag," you say, and your body quakes underneath the covers. Your face is so hot, thinking of how he looked at you so hungrily, how he saw your body vulnerable, how the both of you had now seen each other in _various states of undress_ — _this type of thing just doesn't happen!_ And it especially doesn't happen between unassuming students and their _ridiculously_ good-looking teachers.

"I can't even begin to describe how sorry I am," your Professor says, "I heard you talking to somebody and I thought you were with someone — so I just assumed you would be, erm, fully-clothed…"

You make a very startled noise and pull the covers up to your chin in embarrassment. "You were listening to my conversation?" You peep. Your voice is hoarse.

"No!" It's the first time you've seen the ever-suave Professor Winchester look so distressed. "I just heard a small fraction of it when I was walking through the back-yard. I kind of got tangled up in the rosebushes." Up until this moment, you hadn't thought it would be possible to drown in air, but the tension is so thick that you're starting to feel choked.

You’re biting your lip so hard that you think you may draw blood. Breathing out a sigh, you ask about the most prevalent thought on your mind. “So you heard the part about the, the—?"

“Vibrator, yeah… I heard that bit.”

"Professor!"

With a sense of urgency, Professor Winchester licks his lips, and you can see the rising and falling of his broad chest. You wonder if inside those ribs there's a heart fluttering out of nervousness, out of lust, or perhaps both. You wonder if you might ever get more than a voyeuristic glimpse at the luscious skin just underneath his extremely flattering clothes. 

Your eyes almost cloud over into a daydream before he breaks the silence and pulls you back into reality. "Well, I should probably get going…" And he turns to depart slowly, as if leaving some room for you to possibly object. You say nothing, you just watch him and you don't move, you don't make a sound. You desperately want to say something — you want to turn back the clock and start the whole day fresh, you want to forget the entire day's events — but you can't. Your words are falling silent before they even reach your lips. He turns to you. "You know, I was—"

"—yes?" You interrupt a little too readily, not wanting him to leave but at the same time never wanting to see him ever again. Your attraction to him is starting to bleed through your skin. You clear your throat. You didn't mean to sound so eager. "I mean, ah. Yes, professor?"

"I was— I was wondering, if…" his eyes dart from your own to your nightstand. "If… that's… the aforementioned vibrator."

His lips have a naughty, sadistic twist to them. Your jaw drops as you turn your head painfully slow, comically almost. You're thinking _no, please, no, God, please not let that be my huge seven-inch vibrating dildo…_

Murphy's Law.

Laughing in a pitch that is about an octave higher than normal, you try to ignore the embarrassment eating at your stomach lining. You reach out towards it and shove it under the covers, shaking your head all the while. "No! That's my… um— that's something else. It's a, like, it's a lamp that a stupid friend gave me. I know it's trashy… sorry you had to see that. Professor."

For what feels like the hundredth time today, you feel like crying. He looks taken aback, like what was meant to be a playful remark has seriously gone awry. As you two are looking at each other with no words exchanged, you think that maybe he "bought it" or at least he'd be kind enough to erase it from his mind completely, and then the thing starts _fucking buzzing_ under the covers. Quickly you turn it off, trying to ignore the smirk on your teacher's face. 

"A buzzing lamp?" He asks, looking like he's trying not to break into a grin. You breathe in weakly.

Your eyes are downcast. "Attention to detail," you say, and at that you start to feel a smile coming on. The whole situation is so unreal that it's becoming funny. Like when water is so cold it burns — you're so terrified that it's now comical.

"I can see that."

**Notes for the Chapter:**

> What would you do if the Professor saw you almost naked? Oh boy...


	7. Humdinger

**Summary for the Chapter:**

> Mr Winchester is both charming and so very unprofessional at the same time. Let's just see where things go, shall we?

**Notes for the Chapter:**

> I know, I know! This one's terribly short. But not to fret - the next chapter definitely makes up for it. The reason it is short is because I had to tie up some loose ends. So, it's more like chapter 6.5 than seven. Trust me, it won't be a regular occurrence. Stay tuned for lengthier, juicier bits! 
> 
> And you know what they say: good things come to those who wait.

A moment's silence, and then the two of you burst out into laughter. Professor Winchester has his hands over his face, laughing heartily about the complete absurdity of the situation. You shake your head to yourself, grinning like a madwoman, and breathe out deeply.

"I've accepted the fact that my life is completely out of my own hands for the time being," you say, and the man in front of you sobers a little, his smile softening. You suppose he can relate.

This time, he turns to leave for real. "All things considered, I'm happy to go along for the ride," and there's that decadent voice again, "listen, I've gotta make all this up to you sometime — how about we grab something to eat on the weekend?"

 _Is this a date?!_ You try to play it cool on the outside, your eyes betraying no fluttering of your heart. "Sure, yeah, that's... dope," you say, and you cringe as you sound so obviously not-cool. He doesn't seem to mind. You bite on your lip, and his eyes languidly caress a trail down your face, his expression flushed and demonstrating visible restraint. You swallow.

He clears the air. Looks around. Looks everywhere except at you.

"Ahem. Excellent, just, uh, text me about it whenever," is his reply, and he's already half-way out the door before he kicks you when you're down, "have fun with your vibrator."

That little humdinger makes your ears _burn_. You feel hot, tendrils of embarrassment snaking around your hot throat. Your arms reach for him before you can process what you're doing. Like a petulant child, surprised and teased. " _Professor!_ You can't just— but how will I even text you—?"

But alas, in the blink of an eye, he's disappeared. Scrambling up to see him, you find nothing but your empty backyard. You huff and grab your bag, jumping back onto your bed. While you cuddle your backpack in thought, you feel a hard bit of paper jabbing into you.

"What's this?" You wonder aloud, unfolding a little cardboard square that had been neatly tucked into one of the side pockets of your bag. You grin when you realise it's his number, with a little hand-written message. The sneaky man. How he could be so deft and charming is beyond you.

 

_Prof Dean Winchester_

_I feel like this isn't the last we’ll be seeing each other, kid._

_And that's not just because I'm your teacher. ;)_

You send him an obligatory 'testing' text and clutch your phone to your heart. Your brain has effectively turned to sludge. Stupid sexy teacher. _Just what are you two getting into?_


	8. Telephone Shenanigans

**Summary for the Chapter:**

> Looks like your everyday phone call just got hotter...

**Notes for the Chapter:**

> Oh, I'm sure you've all needed this. Damn, girls! All of ya up in a tizzy for our beloved Professor Winchester? 
> 
> Don't worry. I am too.

It's a Friday night and you're feeling promiscuous. The house is still empty, thanks to your parents getting their tan on in Nouméa, and you'd turned down partying with some of your gal friends to snuggle up on the couch. You aren't exactly feeling yourself — the week's shenanigans have been swirling around in your head all day and night. You're feeling all kinds of jumbled up.

More specifically, you're  _horny._

Stripping down, you stretch yourself out on the couch and let the leather brush your bare skin. You don't remember the last time you masturbated. You let a sigh escape your lips, your hands fluttering over your breasts and stomach. You can't help but imagine your hands being replaced by the sturdier, rougher hands of your drama teacher. With a shaky breath, your fingers dip lower, parting your folds gently to play with your sensitive clit. You can't stop thinking about _him,_ about the way that he fondled himself, about the way that he moaned, how his cock was the most perfectly-sculpted piece of art you've ever seen in your life—

You moan unashamedly, the pleasure increasing exponentially when your other hand gropes your boobs. Your nipples harden as the cool air of the room engulfs you. You use your aching digits to spread the wetness you're creating over your pussy lips, getting the entire area nice and slick and smooth. It feels good — fucking _incredible,_ hot, dirty, _naughty_. You can feel the pink-hot pulse of an orgasm begin to creep up on you, and your arch your back as you mewl and whine. It feels _too_ good, _obscenely_ good, and you're almost there, you're so _close_ , you're about one breath away from a shuddery, delicious release—

_Ring! Ring! Ring!_

Your eyes fly open as you bring your non-sticky hand to your face, brushing your stray strands of hair behind your ear. _Jesus, you can't catch a break, can you?_ You put in your headphones and answer the call, your breathing still ragged and your pussy still throbbing from the erstwhile teasings of your fingers.

"Mmm, hello?" You say, your voice a little more seductive than usual. You're eager to end the call as fast as you can.

"Y/N?"'

You gasp. "Professor Winchester?" _Of course._ Who else would it be? Why is he suddenly infiltrating your life? You let out an exasperated breath that sounds a lot more like a moan, but you don't really mind— your head is too far gone in the clouds, pining for the sweet, crisp release of an orgasm.

He sounds almost sheepish, his voice lilting and only slightly unsure of himself. He sounds a lot more casual than you've ever heard him, and aall of a sudden you wonder what he's wearing. What he's doing. All you can hear when he speaks is that rough, rich voice groaning obscenities; your mind being flung back into that little peeping tom experience that began this whole debacle. "Please, I think we're at the point where you can call me Dean now." After a pause, "am I catching you at a bad time?"

"Kinda!" You admit, and against your better judgement, your hand starts to resume its ministrations. You really are a naughty, naughty girl. "Oh, _Dean,"_ the name tastes like fruit swirls through vanilla cake on your tongue, "U-um, sorry. What did you need me for?"

"I assure you I'll be brief. I just wanted to ask you if you wanted to go out tomorrow," he replies, and his voice is full of honey—  dripping with it, really. You sigh as your fingers dip in between your folds again, gliding over your wet, hard clit. You try to turn your head away from the mic on your headphones. You're not thinking clearly.

"That—" you begin, your voice catching, "—sounds really lovely, Profess— sorry, _Dean_." You can't get enough of that name. It sounds like a choir of angels whenever you speak it. You return to groping yourself and your fingertips singe you, leaving tingles up and down your naked body. Your lungs expand with hungry gulps of air. You're getting close again. This is so many different levels of fucked up you don't even know where to begin. "I've been meaning to text you about that…" your voice trails off into a barely-audible whisper.

And you had been meaning to. You had just felt so incredibly confused and muddled about your whole relationship with him that for the past few days you had thought it best to cool off a little. You hope it hadn't come across as disinterest. It is absolutely, positively the opposite. You are going mad with infatuation.

You don't think he's noticed anything to do with your less-than-professional conduct. "It's fine, really. If you're free I can pick you up tomorrow at four?"

You're gently sliding one finger inside yourself. Cheeky, frisky girl. If he knew what you were doing to yourself… your mind runs wild with fantasies of the man kissing you, sucking at you, _groping_ you in lewd and terribly delicious ways. "Mmmm, _oh that feels good_ — I mean, sounds good, that really f— sounds good to me." Gently, you push your finger in and out, your pussy contracting around it. You could really use something thick in there right now. You picture his delectable body, his perfect cock that spurted rope after rope of come forcefully. You want it all, on your face, on your tits, on your ass, you don’t care— you just want him, his come, you want to be the physical cause of his orgasm, you're so _close, so close!_

"I was thinking of going to the state library or maybe a nice park or something—"

"—sounds a lot like a, heh, date, Prof." You tease him, but you're quite flushed at the thought. Your body is writhing, trembling, and your pussy needs _more._ You slide in another finger, your breathing getting harder and faster. A high-pitched whine escapes your lips. _So close. So unbelievably close_.

"I guess it is, in a way," he muses, voice going straight to your pussy. How was he able to do that so effortlessly? You can hear his charisma through the phone, and it makes you want to get down on your knees and suck him until he blows his load in your mouth. Your slick is dripping down your ass and making a mess of your inner thighs and hand. "But that's all I wanted to say. I'll leave you be. Before I go, I just wanted to ask you one more thing."

You sound almost wounded when you speak next. "Yes?"

"Do you have one finger inside yourself or two?"


	9. Vulgar, You Think

**Summary for the Chapter:**

> Smutty stuff that everyone's been waiting for. You and the Professor have a very unprofessional shared experience. A very... climactic moment.

**Notes for the Chapter:**

> Special mention to all of you wonderful people in the comments who have motivated, inspired and encouraged me with all of your kind sentiments! It truly does mean the world, so thank you for sticking by. I hope you enjoy.

The fingers inside you still, and your body goes into panic mode.

"Wh-what did you just say?" You ask, bewildered; your stomach is tensed.

"You heard me, gorgeous," is his reply, low and dangerous, sizzling through the phone, "how many fingers do you have inside that pretty pussy of yours?"

His words are pure sex, unashamedly uncensored. You feel yourself choking up; hot tears start to form along your lower lids in embarrassment and surprise. "H-how did you—"

"How did I know? _Please,_ sweetheart, _spare me_ — those sounds — the  _noises_ you've been making, shit; did you think you could just get away with that? Like I wouldn't know what you were doing?"

"I'm so sorry — I was already touching myself before you called, and I just sort of didn't want to stop, and — uh, I just, fuck, I… I feel so humiliated right now, I don’t even know what to say, I'm sorry."

A pause. Your body starts to buzz, to vibrate with an electric energy. You can hear him breathing on the other end of the line, heavy sounds that remind you of that ever-mortifying incident that began it all.

"You know, you don't have to stop." He says, pensively.

"Excuse me?!"

"Just… keep going, darlin'."

You enter Nirvana.

 "You don't have to fuckin' tell me twice," you moan, leaving all of your reservations behind you, and your fingers leave your clenching hole to circle at your bud of a clit. You sound sure of yourself, confident, sexy — but on the inside, you're conflicted and stormy. _This is so wrong,_ you think, as you bite on your plush bottom lip. _This is so goddamn wrong but I can't stop._

The loss of control is scary — you're tumbling down a chasm of dark lust, your legs trembling in a mixture of lust and adrenaline.

"What did I tell you about your language?" He grunts, the sound of his own pleasure blistering through the phone. "Dirty girl. Dirty, lovely girl."

You gasp, "are you t-touching yourself?" Dizzying feelings of alternating black and white bliss shoot through you. You're glad you're lying down, otherwise, you're sure you would have toppled over. You are wound precariously; a coil of hot pleasure is inside you and growing tighter by the minute.

"'course I am," is his gruff reply, and you see stars in front of your eyes, unable to believe what's happening. "How can I not wh— fuck, when you're makin' sounds like _that._ Fuck. Yes, doll. Yes I am."

You suck in air through your teeth. "Oh, fuck," you moan, as your fingers move in a figure-eight motion over your clit. "Tell me h-how."

"Don’t do this to me," he whines, and you can just imagine him, his beautiful visage, "I-I'm, shit, pullin' myself off to you. Your voice. Rubbing my s-sensitive cock."

"Prof—" you begin, but stop short, " _Dean._ W-we can't be doing, ah, this." Your pussy wants something to tighten around. "We shouldn't be—" you push your fingers in again, "—doing—" you curl them towards your g-spot, "—this!"

You can hear his laboured breathing through the phone. "I'm so close, sweetheart, are you close? Are you gonna squirt with me?"

 _Vulgar,_ you think. You love it.

"Yes," you say without a second thought, the affirmation coming much too fast — much to his amusement. You are too close for comfort as you effortlessly catch up to his state of arousal when he takes that authoritative tone. "Yes, sir." _Oops._ The title comes out before you can stuff it back in your mouth.

Throughout all of this, he is constantly moaning, cursing, gritting out your name like it's a prayer. Your admission of submissiveness hits something hot in him, and he sounds taken aback. "Fuck! Again, gorgeous."

You are surprised, but you indulge him nonetheless. "Th-this feels so _good,_ sir, you have no idea. I'm so close to the edge. I'm so, so close sir. Are we gonna come together?"

"Fuck, fuck, fuck, keep going, I'm gonna spurt," is his rushed reply, and the words you're hearing start to swim around your head and become muddled. Your body is on fire, tingling with pulsing heat, and you prepare yourself for the inevitable, imminent, earth-shaking orgasm. "I'm gonna fuckin' come, I'm gonna come—"

"—I'm gonna come," you say, your voice intermingling with his.

"Oh, I'm coming," his chocolately voice peals through the phone, bouncing around in between your eardrums, his moans following the spasms of his body. "Hhng, h-holy! Fuck! Baby!"

But you can't hear him, because you've entered some sort of new state of being. Your orgasm hits you, knocks the wind out of you; your stomach contracts, the coil inside you snaps, the slick gushes down your thighs, your pussy leaks with every spasm. You're aware of a voice shrieking, and only after a few disorienting seconds do you realise it's your own. You're babbling obscenities, praise, blasphemous words— a seemingly endless stream of incoherent thoughts as you orgasm relentlessly. Your vision goes dark.

When your orgasm finally ends, you can't speak. You communicate in hums and grunts.

"Wow," he says, after a while of letting the white noise bounce between the two of you. "I'm gonna… need to… do a re-evaluation of my life now, " he laughs. You hum in amusement, but the release in you is so strong that you feel almost like you could burst into frigid tears. A total, full-blown, emotional release. "This… is… interesting."

After a while, you have the strength to speak. Your voice is raw, your throat scratchy. "I guess—" you cough, "I'll see you tomorrow."

"Right. At four."

"At four," you confirm, grinning madly. "Take care, Professor."

You hang up the phone, your hands sweaty and shaking, and then you promptly fall into the most restful sleep of your life.

 

**Notes for the Chapter:**

> Leave a lil' somethin' down below if you have a particular request, or if you just wanna say hey. I love talking to all of you, so don't be shy! I make sure to read every comment! :-)


	10. Imposter Winchester

**Summary for the Chapter:**

> The escapades continue. You're as adorable and as confused as ever.

To say you're nervous is an understatement. Hell, standing in front of the door to his house is enough to make you nearly pass out.

There had been a change of plans - he said that he had to attend an impromptu teacher's summit, but he was sure he could duck out early and meet you at his place, so the two of you could shimmy together to a place of his choosing. Not too much of a fuss, in retrospect — but once you're standing at the wooden monolith, fist raised pre-knock, it seems like a huge step forward in your not-so-ethical 'relationship'. _Are you ready?_

_And that's how you've ended up here, standing at Professor Winchester's front door, deliberating for over a minute if you should politely knock or ring the doorbell. What are you going to say? What is he going to think about your outfit? Are you overdressed, underdressed? All these thoughts rush about your head and put you into a stupor, your teeth worrying your bottom lip in thought._

Thankfully, as if on its own accord, the door opens anyway.

But it's not at all who you expect.

"Hello?" Answers a tall — _very tall_ , you correct — lithe man, with delicate chocolately locks of hair and the most piercing hazel eyes you'd ever seen. Or were they blue? Or brown? Almost instinctively, lost in his stare, you go to take a step forward— as if trying to get closer to that colour, to pinpoint the intricacies of his irises. Of course, _you being you_ , your foot fumbles on the doorstep, and you don't realize that you're falling until you're being cradled by the man you've yet to say a word to. You let out a nervous giggle. He smells divine, like vanilla and field flowers.

In his arms, looking into those eyes that you've finally gotten closer to, you say, "hello."

He smiles cheekily, toothily. "Um… did you need something?" Setting you back upright, you rub the parts of yourself that he'd touched when he caught you, and you take in a deep breath to right yourself.

"I'm sorry, I think I got the wrong house," you begin, but the rest of your words die on your lips as you watch his eyes graze your body, up and down. For a second you stand there with your mouth open, trying to piece together something coherent, but when he looks at you expectantly — silently asking you to continue — you come out of it. "I- I- I was looking for Professor Winchester."

"Er, speaking," he says, and folds his arms, and for the first time, you notice his crisp white button-down shirt has its sleeves rolled up to the elbows.  _The same thing that Dean does,_ you think. Confused, you tilt your head to the side ever-so-slightly, and his amused grin just causes you to look even more bewildered. "What did you want from him?"

 _Oh, to answer that,_ you think, and your cheeks heat up as your mind blows up with salacious requests. But you're still perplexed. "You're not Professor Winchester," you say with a curt tone, "I don't understand."

Now it's his turn to look confused. "Last I checked, I was." The awkward silences are becoming too much for either of you to bear. "Listen, come in. I won't have you standing outside in the cold in that tiny outfit — even if the view is pretty nice," he quips, "let's sort this out together. Don't be shy."

You step inside. This imposter Winchester has a nice house, but you really should be excusing yourself. You don't want the real Winchester to think that you've stood him up! "This must be an alternate reality. My Professor teaches AP Drama."

He's leading you into the living room when he suddenly makes a noise of recognition. "You must be thinking of my brother, Dean. That makes more sense. He should be back any time. He's late, actually, for a date. But I guess you already know that, huh!" You blush. _So he told Sam._ You become a whole lot more comfortable once you're sure you haven't stepped into an alternate dimension. He gestures for you to sit on one of the plush couches, and you do so. "Would you like something to drink?"

"Erm, no thank you," you say, even though you're starting to feel a bit parched. Like the polite young lady you are, you sit with your knees together, your hands placed upon them. You look like the spitting image of courtesy — even though the day before you'd gotten off to the sound of your professor mumbling obscenities through the phone. You're absolutely taken aback by the gorgeous, long-limbed man standing in front of you. "I didn’t know Dean had any siblings."

"Yeah, fancy that," the man smiles and takes this moment to introduce himself. With warmth, he moves a few steps forward and offers you his hand. "I'm Sam. Dean's younger brother." You take his hand and marvel at the heat coming off his body.

"Younger?" You muse aloud, "but you're so… big." As soon as it's out, you cringe inwardly and let go of his hand like he's burnt you. "I mean, as in tall. Long… limbs." _Nice save,_ you think sarcastically, but he doesn't seem fazed. He chuckles.

He sits down opposite you, on a blue one-seater armchair. "We get that a lot, actually," he says with that voice as soft as silk, "kinda funny actually. I'm four years younger and about four inches bigger… I mean taller," he adds, and you look away, biting your lip. _What is in the water at the Winchester house? They are both drop-dead gorgeous._ _And they're both huge flirts?_   Are you the luckiest girl in the universe?

"You're both Professors," you breathe, coming out of your thoughts, "that’s neat."

"Got our degrees together, in fact." He leans back in his chair, stretching those beautiful tan arms above his head. "But we practice at different Universities. Too confusing, I guess. And we have different interests."

You can't help but lean forward. "Of course," you say, falling into conversation naturally. "What do you teach?"

"English Literature," he says, and it suddenly makes a whole lot of sense. There's a pause, and the two of you size each other up for a while. His smile dims. "So are you a... student of Dean's?"

Tricky territory. You don't know what to say. You don't know how Sam will react. Perhaps Dean did this often, bringing home students of varying eagerness — perhaps he'd just lied to your face and counted on the fact that you'd never find out. Or maybe this was a first, and Sam would be mortified and disgusted by his brother's behaviour. You choose your words delicately, each one coming out with a great gentleness. "Yes, I'm in his Voice and Body 2A class."

He takes it surprisingly well. "Oh, are you Y/N?" When he says your name, you suck in a hasty breath, because it rolls off his tongue like a dizzying prayer. It's then you realize you never introduced yourself, but it doesn't matter anyway, because you're nodding your affirmative. "Right on. Dean's talked about you before. Says you're an excellent student."

You put your face in your hands. "Oh, my God," you moan, "that's so embarrassing."

"Hey, don't be embarrassed!" He laughs and jumps up to put a hand on your shoulder. "I'm gonna make myself a coffee. Want one?"

This time, you accept the offer. "Yes, please, actually."

"Follow me to the kitchen, and we can chat about all the things that come along with being an AP drama kid," he says, in a way that's totally innocent, but you can't help but think about how  _he doesn't know the half of it_.

"Wh-when is Dean coming back?" You ask shakily. It's not meant to be offensive, but your watch is telling you that it's half past four and you're not sure how much longer you'll be able to go without doing something fatally embarrassing.

"Soon, I'm sure," he says, grabbing your hand and leading you to the kitchen. "But hey, don't look so down — I'm sure we'll find a way to keep ourselves occupied."

**Notes for the Chapter:**

> Dudes, this was sooooooo much fun to write. There's something about Sam that's just so... wholesome. I can see him becoming a main character - possibly meaning a love triangle for the flustered little reader? Who knows what's in store. Remember to leave some love in the comments if you're liking the series, it's always nice to read them when I'm looking for a huge pick-me-up! You guys are the best!


	11. Little Invitations

**Summary for the Chapter:**

> Sam's back by popular demand - even though he never really left.

_His invitations are innocent enough._

"Here's your coffee," he says, all long limbs and fresh cologne, holding a rolled-up newspaper in one hand. He's pure sex on legs, you have to admit, but you're worried about how Dean might react to your sudden affections. Surely he won't be happy with you having the hots for his _brother_ of all people? Even though Sam looks as if he's just stepped out of a magazine, it makes your moral compass spin — and his suggestive looks and grazing touches are doing nothing to quell your roaring internal fire.

The kitchen is luxuriously open — a big dining table to the side and a large space for cooking taking up the majority of the room. Despite the cold from outside threatening to creep in, the room is warm, and the raspberry candle with its flame flickering in the middle of the table is perfuming the entire place with a deliciously decadent smell. The fragrance makes you hungry. It also makes you _other things._

You accept his offering graciously, realising how much you're craving the kick. The porcelain mug sends heat to the palms of your hands. "Thank you." A pause. He's sitting down opposite you, elbows resting on the table, and his body is all that you can see — he takes up your entire field of view because he's so breathtakingly _big_. Commanding, strong, magnificent; you can't help what slips out next. "Sir." Hopefully, you think, as his mouth opens in surprise, you can pass it off as a light taunt.

"You tease me!" He laughs, letting the newspaper fall onto the table with a thud. He opens his mouth but says nothing— it looks like you've really left him speechless for a second. His jaw flexes a few times before he composes himself. "But really. Just call me Sam. Unless, hey, you're into that — professor kink, right?" Sam winks at you disarmingly, a move designed to make you understand he isn't being serious — just ribbing you light-heartedly. But his comment strikes too close to home, and you dart your eyes away from him as you cheeks fill with a dark scarlet. His smile falls, making his entire face look a lot more open. "Oh! Y/N, no stress. I'm just being dumb. You can tell me to shut up at any time. Seriously."

He's so genuine that your cheeks start to hurt from smiling. "Oh, I could never." Your voice is soft and alluring, and you feel your heart begin to flutter. One by one, in your mind's eye, you start to see rainbow-coloured fireworks go off through the frosted-glass patio doors. When your eyes trail their way to his own, the fireworks don't stop. They are uncontrollable, so ready to burst, so excited to show off their colours — staring into his ever-perplexing irises is like watching fire, just mesmerizing. Your heart is singing. You've got to break the tension before he finds you out. _Stop. Spiralling._ "So— Sam. Uh. Tell me about Dean."

He breathes out and you watch his chest compress. You want to rest your head directly above his heartbeat— your intrusive thoughts are turning your brain into mush. "Where do I start?" He rests his mug on the table, stretching his arms above his head. His sheer _size_ is enough to make you swoon, to intimidate you, to excite you — he honestly looks like a mirage in front of your hungry eyes, something you could only dream about in your wildest fantasies. "He's my everything, honestly. Basically raised me. He's super charismatic - stubborn, though. But a real authentic guy... he also has great taste in women…"

"Oh yeah?" It's hard to deny the fact that you love being lathed in attention and compliments. His words — they're unadulterated music to your ears. You push his buttons. "Are you sure you aren't just saying that, Sam?"

"I'm absolutely positive," he exhales, leaning in towards you. The air around you two is swirling, fireworks still exploding, the music swelling— you lose feeling in your legs. Lucky you're sitting down. " _You_ are the most gorgeous young thing I think I have ever seen in my life."

Your mouth is dry — you're constantly having to re-wet your lips, and his eyes never miss the action — blue-green-brown darting down to commit the path from your pupils to your lips to memory. "You tease me," you say, echoing his previous statement. But there's no humour in it— the tension has sucked all the ease out of the room. You're both made of clenched muscles and increasing heartbeats. _How do you break the tension?_   "Is that today's paper?" You ask. Good. Be neutral.

"It sure is. Come sit here, and we'll read it together."

_His invitations are innocent enough._

"Next to you?"

"No, on my lap." He pats the thickness of his thighs, clad in those flattering dark slacks. When you start to laugh, he stares at you with hard, cool eyes. It takes you four awkward, diminuendoing chuckles to realise that he is actually challenging you — gauging your reaction with a predatory smile. "Come."

It's automatic. "Okay." You stand up and make your way around to his side. He makes room to accommodate you, and there is only a brief moment of hesitation before you seat yourself right there on his lap. He's so warm — unfairly so, burning hot and with a persistence — and he is really, very comfortable. His arms are on either side of you, caging you in, but you feel safer than ever.

"Always so obedient, Y/N?" He laughs, and you feel the faintest hint of his breath on the back of your neck. His fingers touch your back lightly.

It's hard to keep your composure. You're sure you're shaking, and you're sure he can feel it — you're grateful that he doesn't mention it. "Only when you use that tone of voice."

"That professor tone of voice? You like that?" Your panties are dampening with each word that comes from his sinful lips. All he knows is how to exude this deep, lustful magnetism and nothing else. It feels like even his _words_ are caressing you.

You're kind of falling apart. "Maybe a bit."

"Oh, I picked your poison right away, didn't I? Professor kink?"

He ignores the squeak that comes out of you. "I mean, heh— you're also unbelievably fucking handsome. I'm sure you invented the professor kink."

Sam laughs. It's a laugh filled with pure amusement; it sounds simply orchestral to you. "What a mouth on you…" he trails off, and pulls you closer to his chest. "Come on, rest your full weight on me. I'm a big, strong man. I can take it. We'll read the paper."

"I am resting my full weight on you," you say, turning yourself slightly to look at him. His eyebrows are creased, and your face starts to mirror his.

"Really?" You're not sure why he's so surprised. "God, you're so small! My little baby thing! I don't believe you."

"Truly!"

"Take your feet off the floor, then, really relax completely into me."

You do as your told, your cheeks heating up. It takes a bit of balancing, but after righting yourself by straddling his legs a little more, you're able to rest yourself on him so that your feet _just_ miss the ground. He grunts, shifting his hips — presumably to find a more comfortable position — and finally, you two settle on him keeping his legs together, while you spread yours more than what's probably decent in your little skirt. In this position, with his head resting on your right shoulder, you do feel like his little baby thing— and you're painfully aware of the fact that your attention-seeking clit is resting pretty neatly on the crotch of his pants. Fuck. _Fuck._

"Are you flirting with me, Sam?" You ask, as his lips dizzyingly graze your neck, his hands clutching your arms almost subconsciously. You hear him breathe in through his nose.

"Me? Flirt? Never," he says, and his hands switch it up to rub knots out of your shoulders. You sigh. "I couldn't. You're _Dean's_ girl, aren't'cha?" His hips start to shift under you, and you bite your lip — your clit starting to feel a little stimulated under the innocent ministrations. "Hhnng— he's gonna be— fuck, back soon." You're pretty sure you've drenched your panties and that your wetness is leaking onto him. "He wouldn't like it if he came back to me— nnngh— with my hands—" those devillish, hot hands are rubbing your lower back, now, and moving around to your torso, playing with the flesh available to them, "—all over'ya. Trust me, this is totally friendly."

You know exactly what he's doing but you don't want him to stop. You never want him to stop. You shift some of your weight onto your forearms, which rest on the table, and gently you push your aching clit over the bulge in his pants. He's getting you off and he knows it. You know he knows. He knows you know he knows.

"Are you always this friendly with company?" Your question ends in a much higher tone than you're expecting, and his hips shift again to give you that friction that you're craving.

"No, Y/N, no — God," he's finding it hard to stay poised, you can just tell, and it makes you feel a little better about your own state of total discomposure. "Not at all. Fuck…"

"Please, don't stop being friendly," you say, in a voice just above a whisper, and he groans out in aroused frustration. "Please don't stop."

"Up a little," he says, and one hand grips the back of your upper thigh while the other starts to undo his belt. You have no idea what he's doing until he's got his cock out and he's rubbing his head along your achingly wet, cloth-covered slit. "Stay there. Can your muscles hold you?" All you can do is nod. "Great. Now let's read the paper," he says. Most of your weight is displaced on the table, and you're sure now that your slick is running down your thighs. He can feel it. You think he likes it. "Today in sports — some guy kicked some goal. Fans go _wild._ Don't you think that's interesting?"

"Y-yes!" You exclaim, eyes rolling toward the back of your head. He slips your panties to the side so you can feel the hot skin of his cock rub your clit up and down. Your toes find the floor again, and it gives you more leverage to move — his cock moves up and down, up and down, hitting your clit over and over in such a stimulating way that you know you're not going to last long. In the back of your head, you hear a click, but all you can focus on is his dick and the gorgeous things he's doing with it. Sometimes, to tease you, he'll dip down lower than usual, and his cock will almost be sucked in by your tight little pussy, but he pulls away quicker than you can sit on him, and moves right back to that little sensitive nub of nerves.

"Nothing much to see in sports today. Let's look at the weather. You reading with me, babe?" He asks, voice comprised entirely of male dominance and mockery. "Interesting. It says here that it's going to be a little _wet_ today." With a sigh, he slides the head of his cock inside you, and your quads stiffen — your body writing in ecstasy. "Hopefully though, we can keep you warm in that tiny little outfit — all warm and ready for when Dean gets home. Yeah?"

You know he wants a response, but you've got no words left in you. All you do is sigh, moan, breath, sigh, moan. "Mmm—" Some type of jingling noise. He pushes himself inside you a little deeper.

"I'm awfully close, sugar," he grunts right into your ear, and he exacerbates the statement by tensing his cock and making you twitch. "You want me to come inside or out?"

"Out, out, outside," you say, to the beat of his thrusting, which stays consistently rhythmic unless he gets too close to the edge and has to go back to shallow fucking. "I wanna see it— I'm obsessed with— come, I like, I think it's hot to see men come—"

He's completely breathless and sweating like hell. "A professor kink _and_ a come kink? Did Dean hit the fucking jackpot?" A deep laugh, but you can't pinpoint where from.

At Dean's name, you feel a pang of guilt, but you're too far gone now. "Hhh— I'm gonna… Sam, p-p-please, I'm really— gonna… if you keep—" your body is melting, seizing up, turning to jelly and hardening again. You're going hot, going cold, freezing — you have to scrunch your eyes shut as your pussy starts to contract in orgasm, "I'm fucking coming…"

"Yes! Yes! Yes!" He's got a particular way of thrusting that pushes up against your G-spot, and you start to jet a clear liquid from your pussy in the crudest of ways. Sam grips onto you fully now, pulling you back so that your squirt sprays up vertically into the air, looking equal parts depraved and absolutely lewd. "Lemme fuck the squirt outta you! Oh, shit, fuck— I'm gonna…"

Sam pulls his cock out and starts to move it back up and down your clit, giving you that overstimulation to make you shake and whine. But you can't move — he's got his massive forearms wrapped around your torso, and with every shift of his body he readjusts to keep you in place. He forces you to experience that earth-quaking pleasure, that ground-shifting touch, for as long as he can stand it — and suddenly, you feel a pulsing, and his hot, hard, mushroom head is jettisoning scalding hot come. One, two, three, four — it doesn't stop — he keeps orgasming, grunting out his pleasure, crushing out obscenities on your neck with his lips, twitching against your clit and making you squeal.

For a moment, the both of you just sit there, together — slumped against the back of his chair with heaving chests.

"Well," comes a deep, hungry voice from the other end of the room. "That was certainly interesting."

**Notes for the Chapter:**

> All aboard the Sam train! Next stop: never. Remember to leave something nice down below! I love reading all of your gorgeous comments! Anyone fancy reading the paper with Sammy?


	12. Ecstasy in Two Pairs of Hands

**Summary for the Chapter:**

> "One word: Threesome."

"Oh, big bro," Sam is panting, slumping forward at the sight of Dean, nearly crushing you under his weight, "when did you get here?" You're blushing so hotly that you think your face must be _literally on fire,_ and the shame coursing through your body is so strong you're scared your tendons might snap from clenching your muscles so hard.

Dean's face is marblesque — his jaw is tight, flexing while he chooses his words. Head lowered, eyes glowing with a ferocity: he doesn't just look like a deity — he is one. When he speaks, he avoids the question. "You know I get jealous, Sammy."

Your pussy throbs in post-orgasmic bliss. Your panties are absolutely ruined, covered in come from both you and Sam. They're so sticky that you have to take them off — silently, you try and do it as inconspicuously as you can, but when they roll down your ankles and _thud_ onto the kitchen floor tiles, you know you've been found out. Sam grips your arms tighter than before and snickers behind your back.

"Ah, yes. I did mention that." You hear Sam chuckle louder from behind you, and he lets up just enough for you to squirm out of his hold.  You jump to stand upright, but your vision is hazy as the blood pumps around your body. You sway. Your skirt is way too short to be going sans panties, but it's all you can do. To your left, you hear the metallic clanging of a belt as Sam re-adjusts himself as he speaks. "I'm sorry, I couldn't control myself. When you said she was _'a pure bombshell babe'_ I didn't realise you meant she was fuckin' supermodel material."

Dean takes a step forward. "Heh, yeah." You can't read his expression. His fists are clenched, and his eyes are still smouldering, but there's something about the wetness of his lips that's making you feel as if you're missing an integral piece of this entirely fucked-up puzzle. "But that's not all I said, Sammy. I also said that she's _the hottest piece of ass you'll ever see,_ and _if you meet her you'll want to rip all her clothes off_ … though I can see she isn't wearing very many clothes at the moment." He redirects his attention to you for a second. "Were you trying to impress me, sweetheart?"

You can't answer him. You feel ashamed, dirty, unholy; your gaze falls to the pristine, alternating black-and-white tiles. Sam perks up from next to you — "it impressed me!"

"Yeah, and you _pressed_ yourself into her, didn't you? Even though I wanted her first? I'm pretty sure I made myself clear when I said _you'll feel yourself pop a stiffy when you hear her say your name._ How much more specific did I need to be with you, Sammy? Besides flat-out saying, _she's a vixen,_ goddamn it, _and I get to squeeze my cock into her first_? You fucked up, boy, big time."

"I'm sorry, Dean," says Sam, and he loses a little bit of that carefree charm he'd demonstrated earlier. His tone is genuine — he truly is sorry, you can just feel it — and with a long arm, he gestures towards you. "She's all yours now, bro. Don't be mad."

Dean takes massive strides forward, clearing an intimidating amount of space in only a couple of steps. "I couldn't ever stay angry at you, Sammy. I suppose she really is a temptress…" He looks down at his brother, staring into his eyes—

"You know I'm still here, right guys? 'Cause you're just, sorta like, talking _about_ me— but I'm… still… here. "

Sam stands up, giving Dean some type of look, and then walks towards you when Dean nods. Damn siblings and their silent communication. "You are indeed," he says, "and what a sight it is. Hair messed," you self-consciously go to touch your hair, to salvage it into something presentable. "Cheeks flushed — lips bitten — such a vision, Y/N. I fucked you good, didn't I?" You don't answer him, but the wetness trailing down your thighs is a dead giveaway. "I think Dean would agree that it'd be a shame to let a hot young thing like you slip through our fingers."

You take a step back as he stalks towards you. "Wh-what do you mean?" You stutter, failing to grasp any meaning from his words. You look towards your professor for clarification. "Dean— you're not mad at me?"

"I'm more... _excited_ than anything," he says darkly, and it's then you notice the growing bulge in his pants. "Listen, sweetheart," and now he's walking towards you, too, and there is a prevailing sense of suffocation in the room, "we both want you. _Obviously_ , you both want us." When he stresses the word  _obviously,_ your eyes flicker away from him in embarrassment at the Sam time that a huge grin stretches across Sam's face. "So, let's just put two and two together. Or, should I say, two and one."

Your mind is swirling at his suggestion. "Y-y-you guys would be okay with that?"

"Hmm…" Sam is humming, biting his lip as he checks out Dean from head to toe. "You of all people should know how hard it is to resist Dean," he tells you, smiling playfully. "I'm pretty sure his beauty transcends all standards of right and wrong."

Dean looks over at him sharply. "You're getting sappy on me, lil' bro. Don't sell yourself short." Something tells you this is not the first time they've been _involved_. You couldn't care less. Two of the world's hottest men — it makes sense to you that they might indulge in each other's touch. And the fact that they wanted you as a third is both daunting and exhilarating.  "So, Y/N — what do you say?"

 _What do you say?_ There's only one answer ricochetting in your head. "I say _fuck yes,_ " you breathe, and in one step you've flung yourself into Dean's arms and you're kissing every inch of him that you can find — his cheeks, his neck, his chest — and in under a second you feel the presence of another body behind you. "I don't care about going out," you say, frantically lifting your little shirt over your head, "have me here," you're undoing your bra clasp, "take me here," you're pushing your skirt over your hips, "fuck me, please. The both of you."

"I've been dying to hear that since the moment I met you," Dean murmurs, picking you up in one fluid motion and carrying you to what you assume is his room. "We're gonna take such good care of you, baby. Look at you. Aren't you cold?" He glances down at your nipples as he asks his, and his question is answered in the hardening that follows. "Don't worry. We'll keep you warm. Just relax." He drops you on his big, roomy bed.

"Take off your clothes," you say, looking between the both of them. You're starting to feel way too exposed being the only one undressed. "I wanna see you two."

Sam climbs into bed as various articles of clothing go flying. "Look at you," he says, his voice more impish than Dean's — but soon, it darkens with an authoritative lust. "In bed with two respected, esteemed professors. Devilish girl…"

"You're doing that on purpose," you whine, and your fingers go down to start rubbing your pussy. "That voice… you're using it on purpose."

"Right, I heard you had a professor kink—" Dean is moving to settle his head between your legs, still not fully undressed. "Now that is very convenient. Maybe we should get the entire faculty of staff on you, Y/N…"

You gasp when he moves your fingers away and starts to lap at your soaked pussy. It's still wet with Sam's come, but he doesn't seem to mind. "You both just love to tease," you say, your voice breathless and sounding like the personification of sin. "What's happened in your lives to make you both so utterly depraved?"

"How much time do you have, babe?" Sam jokes, but his voice quietens as his lips find your neck.

Dean sucks lightly at your clit — the perfect amount of pressure to start getting you closer to that sweet climax — making you rock your hips rhythmically to aid stimulation. "Oh!" You exclaim, eyes squeezing shut, "that feels _amazing_!" Your moaning is exciting Sam again, and you're surprised when you feel a hardness trying to coax itself into your hand.

You clasp your fingers around Sam's length, and he sucks in air through his teeth as you begin to pump your hand. You pause for a moment, stopping to spit — "heh, nice" — and then you continue your stroking.

That man's tongue is doing amazing things to your body. He puts two fingers inside you, touching spots that you didn't even know you had. Since you've already had one orgasm, the next one is quicker to approach, wracking through your body with an obscene intensity and making you arch your back as you tremble. "Please! D-don't! Stop!" You exclaim, letting the climax wash over you fully, and Dean obeys you, making sure to keep his tongue on your squirming, throbbing clit. Your pussy _floods_ with wetness. The smell of arousal fills the room.

Sam, you find, is a very aurally-inclined man. "Shit," he says, after having heard you come apart at the seams for the second time that afternoon, "I'm gonna fucking come too…"

You take your hand off him, though, making him groan. "Not yet, Sam," you plead, and your timing is so precise that he spurts a clear jet of pre-ejaculate, but doesn't tip over the edge into an irredeemable climax. "I need you a little longer."

" _And_ you're into orgasm denial. Fuck, move in with us," he grunts through a scrunched-up face. His cock bobs with effort, streaming continuously with pre-come, and you smile toothily.

Dean's shifting his weight and finally removes his tie and shirt, leaving him naked. "You taste so sweet, baby." He's licking his gorgeous pink lips.

"I bet you say that to all the girls," you manage to sigh out through your thoroughly-exhausted body.

He grins, sucking on the fingers that he touched you with. "Oh no," he replies, and he's lining up his rock-hard dick with your quivering entrance, "I really mean it. Sweet like candy. Sweet like… sugar and spice and all things nice."

"You've sold me," Sam says, "I want a taste…"

You see stars in front of your eyes when Sam leans over and kisses Dean passionately on the mouth, moaning as they share in your taste. You barely have time to react or even recover because even as Dean's mouth is attached to his brother's, he pushes his thick, hot cock into you and it slides all the way in. " _Fuck!_ " The obscenity bursts through your lips, " _Professor!_ "

Sam and Dean both break apart at this exclamation, turning to look at you with amused faces. "Did you hear that, Dean? She just called you Professor." Your body is too used and limp to activate any muscles, so Sam pushes his cock into one of Dean's large hands.

"I did hear that, Sammy. Interesting. So you wanna be fucked by _Professor_  Dean? You want this little fuckfest to go on your report, sweetheart?" Your moans sound like a mix of pleasure and pain; the sensations are twisting to add to your cosmic gratification. "Want me to write, _not only is she an excellent student but she has the tightest, wettest pussy_? I can't imagine how that would go down at the staff meeting. _Very bright, very enthusiastic,_ and _knows how to take cock like a pro?_ It's just filthy, Y/N. _Has a prosperous future_ but also _squirts when she comes?_ "

"Y-y-you're not fair," you babble, and he fucks out another orgasm out of you. His dirty talk is too much to handle — your climaxes are just dripping from you now. "I've wanted you to fuck my brains out since your Introductory course last year— and that — lust… never went — away…"

"Oh, you should have said something sooner!" Sam chimes in, still keeping himself as close to the edge as possible. His cock is a deep red colour, thick and glossy as Dean pumps his brother expertly — with a practiced efficiency. "Dean would never shut up about you. Always talking about the things you said or the things you did— how cute you looked that day. I was always telling him, _get over it, man!_ You're her _teacher!_ It's entirely unprofessional. Could get you in a _lot of trouble._ "

Dean's thrusting gets more erratic as he looks down at you. You can tell he's not going to last much longer. "You're embarrassing me," Dean grits out, playing the straight-man to Sam's racy confessions. 

"Don't be so coy," Sam responds, and his hips began to stutter, the times between his stopping and starting getting quicker as he gets increasingly close to coming. "I remember that time you came home hard as a rock because you saw her naked or whatever in her room. That was a whole moment. Took you three separate orgasms to stifle your aching cock."

Dean's reaching his peak. "In her _underwear,_ " he corrects, "and forgive me, Sammy, for finding the situation hot while she was talking about masturbating to me!"

"Still can't believe you heard that," you pant.

"Naked, underwear, whatever," Sam voice is more strained than before. "You were so riled up that day. Jumpy. Lovesick. I dunno. Pushed me up against the wall and kissed me until I was dizzy with lust. I thought, _fuck, he should see this chick more often._ And you were wild like an animal that night…"

Then, a magical moment.

"Sam, I can't believe you—" Dean's cock is almost exploding, his ballsack drawing tighter to his cock. "I'm gonna—"

"Shit, shit, I'm gonna come—" Sam is bucking his hips into Dean's hand, now, his dick straining.

You honestly hadn't thought it possible, but you begin to have another orgasm. "M-me… too—! Ohhh… f-f-fuck!!"

A triple orgasm. Simultaneously.

Dean, as he comes, pulls out of you, coming in thick, powerful spurts all over your chest and stomach. He groans, pulls himself off, moans, breathes your name, and then moves his fingers from himself to use both of his hands to drag out both your own and his brother's orgasm. Sam comes finally, after being on the edge for so long, and his thigh muscles shake and spasm with the effort to hold him up. You imagine he's all but empty when he finishes, as the sheer volume of come is enough to make you clench your pussy in absolute desire. Too hot. The scene unfolding before you — it's too hot. It's vulgar. Sinful.

And yet it feels so absolutely good.

"Oh, my God," Dean huffs, using his forearm to wipe the sweat from his brow. "Fucking amazing." Sam can't hold himself up anymore and he topples down next to you, all tan limbs and sweet-smelling skin. "This— needs to be a regular occurrence," he concludes, and your heart buzzes. "But for now — we sleep." 

**Notes for the Chapter:**

> I love the way Dean and Sam are turning out in this fic. They're both so playful and teasing! Let me know your thoughts so far. Probably my favourite chapter of the lot!


	13. Meditate Sometime

**Summary for the Chapter:**

> You catch up with Cas and have a falling out with Dean.

Bodies are bustling around you trying to get where they need to be. You feel flushed, out-of-place, like an imposter in a swarm of people you used to call classmates — they don't know what you know. They haven't felt what you've felt — and it makes you bubble with pleasure, with anxiety, with lust. It's a wonderful day, with sunshine littering the ground in hot paint-splashes, and the spring buds blooming in a fragrant whirlwind of colour. You breathe in the vibrant scene and feel your veins start to surge with energy. You are ready for the new week.

"Y/N!" You hear, and it's that familiar voice that has been so distant lately. _Castiel._ Looking as sweet and as studious as you remember him, he's sporting the ever cliché, 'pen-behind-the-ear' look. His electric blue eyes shine as his gaze falls upon your face, crow's feet appearing when he smiles at you. For a second, you're swept off your feet. He has this radiant beauty that takes you by surprise often, an angelic sort of stare that frazzles you. "You seem quite refreshed," he comments in that soothing voice of his.  

You wonder how it's that obvious."You don't know the half of it," you confess, tugging with your thumbs on the straps of your bag. "It's been a crazy week." The two of you walk into the cafeteria to grab a coffee before class, squeezing around the other caffeinated students.

He brushes shoulders with you as he walks, and you try not to take notice of it. He smells good, too — like eucalyptus. "Is that why you've become almost non-existent online?" He's looking at you funny, like he's trying to figure you out. He runs his fingers through his hair as he studies you, perfectly tousling his brown locks. "I've missed you."

A pang of guilt spreads like poison through you and you feel your heart skip a beat. "Yeah. Missed you, too," you say, and you mean it. "I don't— I don't even know where to begin, to be honest." You turn to the cashier at the little hole-in-the-wall coffee shop and place an order for your favourite drink, and add a café latte for Cas. He smiles at you and you guys wait in semi-awkward silence.  As you take both the beverages, "thank you! Keep the change and have a lovely day."

"Woah," squinting his eyes at you as you hand him his drink, "you're in a really good mood. What's up? What's been going on in your life recently?" Slowly, he tries to pry from you the reason for the sudden bounce in your step.

All at once, flashbacks of your lewd acts over the past few days with both the _Winchester_ brothers flash through your mind. That initial threesome to start it all off. Then fucking both of them the morning after. Then going out to a steamy dinner with Dean. Showering with Sam. The pleasure never stopped. It just kept rolling through, rolling through. You don't want it to end — and so you can't let it slip to _anyone_ just what you had been getting up to behind closed doors. Not even your closest friend. Who knows how much trouble they could get into for an illegal, incestuous, teacher-student polygamy? It hurts your head to even try and justify the morality of it all.

Against every bone in your body telling you not to, you have to work around the truth. "Nothing much. I've been uh… you know, taking it easy. Finding myself. Um… meditating?" Technically, you aren't lying, if he can telepathically read your mind to understand that _meditating_ is more like a euphemism for _having unbridled kinky sex._ You suppose there are similarities between sex and meditation, but the guilty, honest part of you knows a half-truth is still a half-lie. You know that somewhere down the line you're going to have to make it up to him, for being both an unavailable friend and also for keeping him so removed from your darkest confessions. 

"Oh. Huh." He takes tentative sips from his recyclable cup. You're almost sure he can see right through you, but he still looks so genuine, so unguarded. Your heart is failing to beat steadily. "Maybe I should follow in your footsteps. I've been feeling very stressed lately with this huge history project."

Heat rushes to your cheeks. If only he knew what you really meant. "Um! Yeah. It's… yeah. Really stress-relieving." You take big gulps from your drink to appear busy, willing the coffee to hurry and start pumping through your veins.

"So tell me about it," Castiel says, genuinely curious, and painfully oblivious. His eyes sparkle with brilliance, and you wince as you understand that you've dug yourself a hole. "The meditation, I mean. I can use all the stress-relief I can get."

You nearly choke on your drink. "Oh, gee, Cas," you're starting to get antsy, checking your phone to will the minutes to tick by faster. You need to get out of this awkward situation! "Um, when you do it… it kind of feels like a really big release. And all the pent-up frustration just rushes out of you. It feels... really good."

He hums, scratching the stubble along his jawline, biting his lip, "Yeah, that sounds really nice. We should do it together sometime. Would you want to do it with me this weekend?"

"Um—!"

"There you are!" You're blindsided by a pair of strong, warm hands pressing on your shoulders from behind. "Not like you to be running late to my class, Y/N. Distracted I see?" Dean's teasing you, but you silently thank whatever higher power there may be for getting you out of this sticky situation. Dean's hands leave you after only a brief moment, and you're reminded to be professional.

"Maybe a little," you admit, smiling at the somehow-crestfallen Cas to cheer him up. "This is my best friend, Dean— I mean Mr— _Professor!_   Winchester. His name's Cas. I've known him for a really long time and he's honestly one of the kindest people you'll ever meet." Cas beams at your glowing praise, and you wink at him

At hearing the words, ' _best friend',_ Dean seems to go cold. You suppose he wasn't kidding when he said he got jealous. As sweetly as he can muster, Dean replies to you, and extends his arm to Cas. "Ah, well you've never mentioned this fine man before!" It's both a compliment and a dismissal of Cas' importance to you — the way Dean can manipulate people blows your mind. Cas, however, is no ordinary man; he can see through the thinly-veiled challenge, taking Dean's hand with a firm grip. They stare each other down. You wonder what the two must be thinking. They're both peacocking — you're rolling your eyes.

"I guess that's because she spends most of her time talking about you," Cas quips, though it's infinitely times more light-hearted. "She can't get enough of you!" At this, you smack your hand to Cas' shoulder, hiding a smirk behind your other hand. Somehow you always manage to be in the middle of all the banter.

Dean's eyes dart to your own, as if to ask, _does he know_? You're taken off guard for a moment. You try to come out of your thoughts. "Um, your class, he means." You interrupt, sobering, and you're slowly shaking your head at Dean. "Your class. I'm really enjoying it, sir. And speaking of classes, I think we are in fact more than late now. Cas, if you'll excuse us?"

Cas shrugs, looking nonchalant. "Of course. I'll see you around, Y/N." Then, curtly, "Professor."

"Don't get yourself into trouble now, Castiel," Dean replies, walking off. You follow closely behind him. "Geez."

"What the hell was that all about, Dean?!" You exclaim, a fire in your eyes. Dean is monolithic, stone-faced and putting out cold vibes. You're not sure what his problem is. "He's just a good friend of mine. No need to be so jealous!"

He scrunches up his face slightly, scoffing. "What do you expect? He's so hard for you, Y/N, you have no idea. I could tell from just that five-minute encounter." Your eyebrows furrow at his lewdness; you have to hide your blushing cheeks from his piercing gaze by looking away. "And it's _Professor Winchester_ by the way. We're _in public_."

"Then keep your vulgarities to yourself too!" You say in a frustrated whisper, hurt by his sharpness. "He's not — oh my god, _'hard for me'_. We've known each other for way too long. He thinks of me like a... a sister, or something."

"Yeah, like a sister he wants to fuck." You wince and bite your lip, choosing not to say anything. "Well, don't make me say ' _I told you so'_ when he confesses his undying love for you. You have to be smart about these things, Y/N. Don't you know anything about men?"

You take offence to the comment. "Apparently not," you say bitterly, creating some space between the two of you. It's at that moment you both walk into class, your forms being met by twenty other pairs of eyes. You clear your throat, moving even further away, pushing his comments out of your mind. It's time to practice now; you have work to do. No time to think — just you in the moment.

He brushes his hands off on his trousers, his usual nervous tic. "Morning class," he says, and you're accommodated into the circle of waiting bodies. You don't look at him. "I see we're all looking bright and fresh today — not too much partying on the weekend, I hope?" A few chuckles from the class. "All right. For this morning's warm-up, we're doing yoga. Everyone close your eyes and let me guide you through today's routine." Nothing but smiles from the rest of the class.

The girls — making up two-thirds of the students in this class — are always willing to do yoga with Professor Winchester. You have nothing against that. Before your  _encounters_ with him, you'd tried to show off too. But _now_ , now it just makes you feel sick, like you're looking into some desperate, twisted mirrors showing you what you once were — and making you realise all of that flirtatious innocence has been replaced by sinful depravity. In child's pose, you wonder if starting these sexual escapades has been the smartest idea.

It's the strangest thing ever, but for the first time in a long while, you feel a deep anxiety worm its way up your throat. It's a moment of depersonalisation, where you scan the room and find that you'd rather be anywhere but surrounded by these people at the moment. Like you're watching a movie, you see your own wilting form in third-person perspective, a total loner in a room full of lithe, energetic thespians roaring to go. You have friends, sure, but they all look like total strangers in that minute of abstractness. You know it's crazy, but you're paranoid that you've got " _teacher-fucker! teacher-fucker!_ " scrawled across your whole body in permanent marker. While Dean has everyone in the downwards-dog pose, you're wondering if you've been corrupted beyond repair.

You're so lost in your own thoughts he has to come and correct your stance. Gently, he pushes on the small of your back, and you feel your body give way to gravity. The pose is easy, you've done it in class a thousand times before — but this time, you're struggling. The touch of his fingertips is hot, but not in a pleasant way — they scald you. You're doing all you can not to jump away from him when he goes to correct the position of your legs and moves the flats of his hands up your calves.

"Professor," you grit out in a voice barely audible, your face blushing hotly. Nobody can see you two since their heads are down and eyes are closed, but you're not sure how you feel about him fondling you in the middle of class.

"Nice stance, Y/N," he remarks, seeming utterly and infuriatingly casual. His hands slide further up your legs, coming to rest between your thighs, and you bite hard on your lip. _Is it degrading?_   You wonder, _being bent over like this, unable to speak or protest as the pads of his fingers move up to gently cradle your pubic mound?_   Against your better judgement, you start to feel wet immediately, the heat between your legs a pure giveaway to your arousal. He moves closer towards you, so the front of his legs are touching the back of yours. "Just let me adjust you…" He says out loud, not wanting to cause any suspicion. Without a word from you, he pushes his crotch into your behind, letting you feel the growing hardness underneath his trousers.

He moves with caution so it doesn't appear like he's grinding his cock on one of his best students. With the most minute, repetitive movements, he ruts against your ass and reaches around you to massage your clit. You're feeling way too hot, way too toyed with and _you'll be damned_ if you have an accidental orgasm in front of twenty other unwitting students.

You shove yourself rather harshly away from him, and he seems to get the message, his body bristling once before moving away from you. You try to keep your eyes closed, but you can't help but peek as he goes around the circle correcting other people, touching girls and boys alike on their backs, their legs, and sometimes their stomachs. Speaking of stomachs, you feel sick to yours, watching him touch them as if he had _special_ relationships with all of them.

Halfway across the circle, a girl calls out, "can you check my stance, sir?" Her voice drips with adolescent lewdness and beauty, and Dean doesn't think twice before moving behind her to examine her pose. You see his eyes darting around her form as he puts his fingers gently on her _ass_ , and you imagine her shuddering with pleasure into the barely-there touch. Is it your right to feel as livid as you do? It's not like you and Dean had had the "what are we?" talk just yet, but it still feels totally inappropriate to you that he'd be doing that sort of thing in class with _other students._ You try to rationalise it — maybe it really is just innocent, maybe the two of them are both unaware of what they're doing, maybe you're reading too much into things; maybe, maybe. But when he starts to caress down the girl's muscly, short-clad legs, you have to squeeze your eyes shut to stop yourself from vomiting on the spot.

The class finishes three hours after that, leaving you sweaty and thankfully more than halfway through with your monologue. You pick up your bag as fast as you can and bolt out of the door, leaving Dean to wonder just what the hell he had to done to be receiving the stink-eye for the duration of his class.

**Notes for the Chapter:**

> Let me know what you think of this chapter - it's kind of a "coming down" from the previous few highs. Gotta experience the lows too or it wouldn't be an interesting plot development! Let me know what you think in the comments below. Never thought this would also be such an angsty story! Don't worry, smut is still inbound.
> 
> And thank you to all the people who have supported this story from the very beginning! As always make sure to leave suggestions in the comment section below, I do read 'em all and try to respond individually to each one. Hope you enjoyed this chapter and look out for another update soon!


	14. Operation Medicine

**Summary for the Chapter:**

> More plot and more plot but more handsome sexy guys! These new characters aren't from SPN, but I was thinking we needed to introduce some of your fellow students! Adds depth, etc. Enjoy and trust me, smut to come!

**Notes for the Chapter:**

> CW: "gay" being used as a slur.

You are generally not a petty person.

But, the day after the incident with Dean, coming back to class is like a slap in the face. You hadn't talked to him that night, instead opting to stay at home crying into a tub of ice-cream whilst ignoring his calls, but you never considered the fact that the very next day you'd have to confront him.

You're sitting there, listening to him talk about the many qualities of "Poor Theatre" — or rather, _trying_ to listen to him talk. You're sure you're staring up at him with hurt, doe-like eyes, but he's looking at you less than normal today. While your head rushes with accusations, hurtful comments and exclamations of despair, a sudden intriguing thought springs into existence — not to get upset, but to get even. 

You are… _generally_ , not a petty person.

But after all, you're surrounded by actors, just as young and lithe and beautiful as you are — why not enlist in their help? The women outnumber the men in the class, sure, but there are still some very attractive guys that you think would be more than happy to help you out with Operation Taste-Of-Your-Own-Medicine.

Dean can tell that his class is antsy to get up and start moving. He scans the room and cracks a smile, shaking his head. "All right, guys, we're going to do an ensemble today. Get into groups of four or five and come up with a ten-minute performance for me. We'll display them at the end of class."

You're the first one to spring into action, jumping up and making eye-contact with one of the hottest guys in the class. You'd spoken to Andy a few times before, but more often than not you had been too shy to move anything past a flirtatious greeting. He looks you up and down, his long eyelashes fluttering over his green eyes, and runs his fingers through his sandy-blond hair. _Wow,_ you think to yourself, _if anyone is gonna make it big as an actor, it'll be him._

"Andy, hey! Do you wanna be in a group together?" You ask with a childish innocence in your voice. There is something about your genuine nature that takes him aback for a second, and then he nods.

He bites his lip to stop the huge smile spreading across his face. Then, "of course, Y/N. You don't mind if my buddies join too?"

Almost like on cue, two other freakishly-handsome men appear before you — Andy's aforementioned "buddies" which seem more like models than students. Luca and Kristian, both more than a head taller than you, and pillars of adolescent flesh, look down at your comparatively petite frame and raise their eyebrows. They have a distinctly European look about them, all hard angles and taut muscles, and don't say anything as you just gaze at them — unable to tear your eyes away. It's insane, really, all the beauty that you are just recently discovering all around you. The more you are able to see, the more that you find — like it is gaining momentum.

As much as your knees feel weak, you have to remain confident. "I could — I don't mind at all," you say, "and actually, that gives me a pretty cool idea," you're hoping the chatter of the other groups will drown out the noise of your devious plan. "I really wanna make a... sensual piece, because that hasn't really been done before in this class. What do you think?" Your voice squeaks as the suggestion comes out. The boys just look at you.

The silence is almost too much to bear. You're being scrutinized for a second, and you're wondering if they're about to call you totally insane when finally someone breaks the quiet. "It's daring," Luca says, running his finger over his plush bottom lip in thought. "I like it. And obviously, you want to be the centre of attention?"

"I—!" It takes you a second to understand he doesn't mean it as an insult, but as a _euphemism_ of sorts. Your face must be a shade of deep crimson because you find all three of them laughing at your expression. "Well, I suppose so, but — it doesn't, like, have to be that way — unless you guys want to do sensual _stuff_ together?"

Kristian scratches at his dark stubble, his grey eyes focussed intensely on you. "Let's talk forwardly with each other, so nothing is misconstrued. I have to say, I'm surprised at this newfound sexuality of yours, Y/N."

For someone that hadn't said more than two words to you over the entire duration of the school year, he seemed to pick you straight away. Andy and Luca nod in agreement, their eyes sparkling with some kind of lewdness. You can't allow them to overpower you, however, so you stand your ground. "People change, I guess," you say, shrugging your shoulders, "I'm taking this newfound sexuaity and running with it," you laugh, "and I'm game if you guys are."

"I'm totally in," Andy says, and you ignore your pounding heart. "So. Something sensual. Did Winchester give us a theme?"

Luca's shaking his head. "I'm guessing it's just giving us a break from our monologues. It's open. How about something surrounding Poor Theatre? That’s what he was talking about today right?"

"That could work," Kristian says, with his dark and introspective voice, "hang on. Y/N, stand there." He points to a spot on the floor, and you follow his instructions. "Now Andy, on your hands and knees. Behind her. Face me when you do."

You're confused, but Luca seems to pick up on Kristian's idea. "Yeah, okay, Poor Theatre. Where we _become_ the props instead of using real ones. Okay. Y/N. Sit down."

Heat is rushing to your cheeks again. "P-pardon?"

"You wanted sensual, right? We're gonna be your props in a 'day in the life of' your character. What does your character do?"

"She's, uh, she's a—" you like improv a lot, but being with three handsome men is clouding your thoughts. Hurriedly, you scan around the room for a faux-profession to give your character. You see a poster on one of the walls advertising for an after-school kickboxing class. "She's a personal trainer."

Kristian's mouth twitches into a tiny, sly smile, "good choice. All right then, sit down."

As delicately as you can, you sit down on Andy's back, feeling his muscles hold you from underneath. He lifts you up a bit until your feet are no longer touching the ground.

Luca's eyes are squinting in thought. "Every professional has to get to their job somehow, right? Okay, you're driving to work in your car. Aren't you?"

"Yes, I am," you reply, and your hands go up to grip an imaginary wheel, your right foot moving between the gas and brake pedals. Andy buzzes underneath you as if he's got an engine in him being put to work. Feeling sorry for him, you lean a little to the side and whisper to your human-chair, "am I hurting you?"

"I've carried football players more than triple your size," Andy whispers back, chuckling slightly. "You're good." 

"So now you're at work. Out of your car," Kristian says, and you do as he says. "As a personal trainer, you need to be getting active with your clients. What are you and your clients doing together?"

You don't want to say it — you're trying to stop yourself from saying it— it's on the tip of your tongue but you're holding yourself back from saying it— "yoga." You say it. Fuck. "We’re doing yoga together."

You are _generally not a petty person._

"Well, do yoga together, then," Kristian replies, and you start moving Andy and Luca into the downwards-dog position. You're about to move away when Kristian tuts and shakes his head. "This is gotta be sensual, right? We're going for shock factor to make the audience sweat. So be sensual."

"That's easier said than done," you breathe, already feeling _yourself_ start to sweat a little. Luca and Andy stay poised in the position you left them in, ever-obedient actors waiting for instruction. You're shaking.

" _It's not,_ " Kristian challenges. "You can make anything sensual. Look." He steps closer to you, looking down into your eyes. He puts his hands on your head to cup your face, his thumbs stroking your cheeks soothingly. You're entranced by his steely grey stare. "Baby, I can see you're bursting with sexual energy. Why don't you take care of that with Andy and Luca, yeah? Run your hands over them, position them where they should be. That's your job as a personal trainer, no?"

"Yes, sir—" it slips out before you can stop it. Kristian's grip on you tightens automatically; almost like you've pressed some sort metaphorical button. His jaw clenches, hard. "Fuck, I mean, uh, what was I saying—? Like, uh, Kristian, I'm sorry, I—"

"Y/N, hogging all the hot guys in the class, huh?" You hear a familiar feminine voice, and it takes you a second to realise it's the girl from yesterday who had asked Dean to " _check her stance_ " even though it was, in your opinion, perfect. You break apart from Kristian for a second to turn to her, your face all red and pulsating with desire, and she looks at with you with furrowing eyebrows. "Since when did _you_ come out of your shell, huh, you ugly duckling?"

"I, I, I don't really—" you have nothing to say, you just want to appear braver than you feel — it doesn't really work.

"Leave her alone," Andy says, from his downwards-dog position.

The girl raises her eyebrows in amusement, and you can see she is partly confused. "Andy, you look totally gay bent over like that; I don't think you're in any position to be authoritative," she sneers, before her face falls flat as Professor Winchester all but looms over her. He's comprised of entirely good-looks and charisma, but when he wants to be, he's a scary motherfucker.

His eyes are cold and dark; eyebrows flat. "Get back to work. You know we don't tolerate bullying in this class, Sabrina." He tells the girl, and she just nods, scurrying to go back to her friends. "I don't want to hear anything of that sort in this class, or you can kiss your pass goodbye. And that goes for anyone in my class, not just Sabrina— but let her be an example of how _not_ to get ahead in show-business or in life, really." Sabrina's fuming. You can't help but smile. For a brief moment, Dean's gaze softens and he turns towards you, but you make it a point to look away. You hear him exhale tiredly. "Twenty minutes to go. Then it's lights up."

You and the three handsome boys spend the next twenty minutes coming up with the most sensual performance you can think of, and you know that when Dean sees it he's going to be unable to keep his eyes or his hands off of you. Your entire plan is falling right into place — once again for the millionth time this month, you ask yourself how you got so lucky.

Dean can tell something's up from the moment you four step on stage.

You are, just for today, going to be an extremely petty person.

**Notes for the Chapter:**

> Remember to leave some love down below! It makes my day and I even get some of my ideas from y'all. Thanks so much for your continued support and I hope this story fulfils all your Winchester needs!!!


	15. Insecurity Breeds Jealousy

**Summary for the Chapter:**

> Your performance doesn't exactly go over as planned. Or does it? Smut, smut, and more smut to come. You know I deliver on my promises ;) Expecting angst???? Take shameless sweetness and sex galore! Mwahahaha...

**Notes for the Chapter:**

> This was super fun to write. I really love experimenting with different plotlines for this story, and also various kinks that I personally like/you guys have mentioned in the comments. And of course, I do listen to your opinions as well, as I saw that a lot of you weren't too keen on the reader being a lil' petty thang. So there's a lot of learning on both parts - both the author and the reader have a joint say in where this goes, what gets focus, who gets the spotlight, etc. It's very humbling and amazing to get such great feedback from so many lovely people - and I hope that over time my writing can improve and take on a unique style of its own. Anyway, thank you for your continued support, and I hope you like this chapter!

"Okay class," a voice says, but this time the voice doesn't belong to your teacher — it belongs to you. You have Andy, Luca and Kristian waiting on your every word as you play out your performance. You're halfway through. "Downwards dog."

The audience is hushed, with an undercurrent of intense concentration breathing energy into your performance. Dean's eyes are burning holes through you, his jaw taut. Your fellow actors obey you, moving into position.

"Will you check my stance?" Luca says, slyly, a line that you made sure would be included in the performance. You nod, as if to say, _of course,_ and stand behind him to adjust his pose. With a sensual slowness, you slide your hands over his back, feeling him exhale underneath your fingertips; your hands continue their journey to move under him, feeling the stability of his core. In your opinion, it's more than stable — you can feel his muscled stomach through his two layers of clothes. His abs twitch as you push up into him.

You bend forward over the boy, so your lips are ghosting the shell of his ear. "Very good," you whisper, just loud enough for the audience to hear. "Such a good student." Dean bristles. You stay in the moment, keeping the audience at a distance. You detach yourself from Luca and say to your ' _class'_ , "bridge pose."

The boys move into the pose, balancing their weight on their forearms and the very tips of their toes. Planking, basically. The move which you can only hold for a couple of seconds they can hold for what seems like hours.

"This is too easy for me," Kristian says, his voice lowering to rile your character up. You squint your eyes, moving closer to his face which hadn't broken a sweat. Your lips are almost brushing — you can see his dark freckles fluttered carefully across his nose.

"Let's move into our final position, then," you say. "Crescent pose. Kneeling."

The boys do as you say, listening to their trustful personal trainer, and then you move onto the next bit of your performance — the aftermath. You finish your ' _lesson'_  and move to the locker-rooms to have a shower.

You turn on the imaginary taps and then the real show begins. In the spirit of Poor Theatre, the boys are acting _as the water_ cascading from the shower head, their hands splayed and running all over your body to mimic the waterfall effect of standing under a shower. You mime washing yourself, floating over their own hands as you move in a joint effort of worshipping you. The scene itself was tastefully directed by Luca — you appear like Venus in a picturesque scene of feminine beauty and appreciation.

As much as you want to be a professional, you note that their hands running over all of you— your shoulders, stomach, chest, thighs and feet — is making you feel warm. Not the _character_ you, but the _real you._ It takes all the willpower in your body to stay present in the scene, and show your bliss actively, instead of succumbing to their touches and their flitting grazes. The audience is buzzing, now, not with words but with raw energy — from the crowd, you can make out Sabrina's face: intensely tight and fighting curiosity.

You turn away from the crowd and their hands continue to wash over you, moving down your back and butt, and you hear Dean's rickety chair squeak as he adjusts his weight. You can tell it's Dean because he's the only one _with_ a chair, as part of his regime is to have his students sit on the bleachers to the side. Perks of being a drama student.

Once you step out of your imaginary shower, the hands start slowing, and they fall to the floor as you 'go back' to being dry. The timing is perfect, because as soon as you finish, the bell goes, and you make the 'curtains down' signal to let the other students know you are finished. However, they don't move— all of them sporting the same open-mouthed, wide-eyed face. They're all fixated on Dean, who has his jaw as tense as anything, and his hands clenched into fists.

When he speaks it's through gritted teeth. "That was… a sight indeed." You suppose he's at a loss for words — you can't tell if that's a good or bad thing. All of a sudden, you come down from your high and wonder if you'd just made the smartest decision. "It fit the theme that we're doing in class, which is good. But in refining, I would say to include less groping, no matter how tempting that may be for young millennials such as yourselves." You exhale. Sabrina snickers. "Class dismissed. Except you, Y/N. You need to stay back for a moment."

"Yes, sir," you say, and watch as the rest of the class file out, now bored. You high-five the other three boys half-heartedly, getting their numbers as they leave, and soon you're alone again with Dean. If you thought _last time_ he called you in that you'd be expelled, surely this time is it. There's an awkward silence only punctuated by your erratic beating heart. "What did you need?" You're the first to say something because all he's doing is looking at you with his face in his hands.

"I'm going to be very direct with you, Y/N. Did those boys use this prompt in order to pressure you into doing something you didn't want to do?" He asks earnestly, his words tumbling out all over one another. He's wringing his hands and the air in the room is exceptionally dry. For a second you feel awful at the sight of him, all vulnerable and undone, and you have to look away, your throat constricting. "Tell me, please, and I will take care of it; I'll do anything, everything that needs to be done."

You must assuage his dark thoughts before they spiral out of control. "What? No! Sir — Dean. It was _my idea._ " He's shaking his head like he doesn't believe you, but you interrupt him as you continue. " _I_   wanted to make the piece sensual. I suggested it! I approached Andy. I just wanted to… well. Make you. Jealous. Kinda."

There's a pause.

It lingers for so much longer than what you're comfortable with. And then, there's a chuckle. Then, a louder guffaw. You seem to have tickled his funny bone. His face, previously lined with anxiety, lightens, and the relaxing of his eyebrows tells you that he's calming down. Indignant, you cross your arms over your chest. "Are you serious?" He asks, his voice laced with disbelief. "Oh, my god. You are precious. I was so worried!"

You're not sure if you're relieved or fired up by his response. "This is not how I was expecting this meeting to go," you confess flatly, eliciting another laugh from him. His eyes sparkle with merriment for a second before sobering up.

"That wasn’t very nice of you, you know. Y/N, don't you think what you did today was a little petty?"

You nod your head, breathing in sharply. You can't look him in the eye. "I know, sir. I acted out of emotion, sue me," you stifle the defensiveness you feel welling up inside you and try to add some humour to the situation. "Nobody's perfect."

He stares at you blankly, blinking for a moment while taking in your entire being with his eyes. "You're damn well close," he whispers, after basking in the pause, and then he pulls you into a gentle kiss. "The closest I've ever seen, baby." His lips are so soft — kissing him feels like coming up for air. You feel more guilty over the fact that he's taking it so well, leaving you as the only person sorely in the wrong.

"I don’t deserve you," you say, and you feel tears prick the corners of your eyes. "I'm so sorry for even suggesting such a stupid idea. I feel like an ass."

His forehead is touching yours, now, and he smiles at you. "Don't talk that way. It was a very clever performance based on the prompt. But I'm not sure why you'd want to make me jealous in the first place? Does this have to do with you not answering my calls?"

You pull away from him and start fiddling with your bag to give your idle hands something to do. You shake your head. "This all seems totally ridiculous in retrospect," you say, "but that girl — Sabrina. The other day when you were fixing her stance in class, with your hands all over her — I got jealous. I just, I dunno, sir— Dean. I thought we had something special?" Your voice cracks. The words keep pouring out. "And it just got me thinking, like, _does he do 'this' with all his students_? Am I just one of many in a long list of saps that you've got wrapped around your little finger? It's hard for me to see you that intimate with other people — I just, well, I didn't know I'd feel so strongly about it—"

"—you didn't seem to mind me being _that intimate_ with my own brother," he retorts. His face is certainly less animated than before, the dim lights in the room lending him a dark, powerful presence.

Your cheeks burn, partly because of the annoyance in his voice and partly because you start to have flashbacks to those wonderful, sinful nights. "Dean, _you know_ that's different!" You take a moment to steady your breathing; he's crossing his arms over his chest — closing himself off from you. "I dunno. It's like, you're opening me up to so many new experiences that I would never have _dreamed_ of before, and… I never considered myself to be embarrassingly jealous, _but here I am_ , and your hands are on Sabrina's _ass_ and I can't bring myself to handle this maturely so I just put on this convoluted play to show you in hopes of bringing you closer to understanding _that I just want you for myself."_

The last part slips out without your brain filtering it, and you clap a hand over your mouth in shock. It's insane, you're saying stuff that you didn't even know you felt, but after it's out in the air you realise it's been hiding in your heart all along. You're not sure how Dean's going to take it; he's just looking at you with a cool, collected face, and you look away because you can't handle his scrutinizing gaze.

"You want to be exclusive?" He asks, surprised, his marble features cracking for the first time. You're still playing with your keychain. "Is that what you're trying to tell me?" He's rattled, smeared with disbelief, and you feel an oncoming wave of emotions threatening to spill out of you.

"I don't know! Is that entirely crazy of me? Is it insulting in the first place considering I'm so lucky to be with you in the first place?" You take his hands in your own, and squeeze, and hope that the tears welling in your eyes don't fall down your cheeks. "Dean, I'm starting to realise that I'm not invincible, and I tried to be all these things that I'm not so I could keep this good thing going. I wish I could be the cool, unfeeling temptress or the delicate blushing flower or the self-assured superwoman but I'm just human—  and— and it's painful to me that you're getting a glimpse of my vices because ultimately I'm fucking _terrified_ of losing you. I don't want this to end, at all, it's just barely started and I'm beginning to feel more and more for you and Sam every day, and it hurts me to hurt either one of you. I guess I didn’t think you'd like me if I showed you all of my anxiety-inducing and awkward flaws so I tried to overcompensate. And so… the short version of all that drivel is _yeah, I want to be exclusive."_

You take out your hands from his and turn away, heading towards the door. Without making a sound, you let the tears roll down your face like tiny diamonds, suppressing the burning lump in your throat so you don't give anything away. Dean says nothing for a second, and you almost think he's going to let you leave without saying a word, before he says, in a voice barely above a whisper, "you _wanted_ me to be jealous?"

You're still walking away, "well yeah, I mean I thought it was hot when we were with Sam so I just thought it would rekindle your desire for me—" as you're talking, Dean takes massive strides towards you and blocks you from leaving through the door, pushing one of his big hands on the flat of it with all his weight. Your fingers are gripping the handle, and confused, you look up at him, only to be surprised by his shadowy and brooding face.

" _Rekindle_ ," he whispers in astonishment and pushes his body into yours so you're pinned against the door. "I _cannot_ believe you just said that." Those soft lips of his start kissing your neck, leaving patches of wetness for you to wipe off in amusement. "My _lust_ ," he pushes his crotch into you, and you can feel the hardening of his cock underneath his trousers, "is always _yearning_ for you, baby, no matter what." His fingers play with the hem of your shirt, and you put your arms into the air so he can undress you by pulling the cloth over your head. Deftly, he unclasps your bra and sighs as your breasts are exposed to the open air. " _I desire you_. Always." His mouth finds one of your nipples and you run your fingers through his hair. "And I suddenly find myself feeling very, very possessive over you… one might even say that I'm feeling… _jealous_." He looks up at you and winks, and you roll your eyes at him, but even you can't stay exasperated when his tongue is doing such brilliant things on your neck. You start to unbutton his shirt, but you only get halfway as he slides one of his hands down your tights, his fingers searching for your wetness. Your dewy eyelashes flutter closed, your mouth falling open in pleasure. Your legs start to feel weak.

He moves away for a moment, extending his hand to you, and you grasp it only to be lead to that infamous desk that started it all. Just like in all those sappy romantic movies, he clears the things from it with his forearm and grabs you by the waist, setting you down on the smooth wood. It's made of an unforgiving material; strong, sturdy, supporting you almost sternly — all the sensory stimulation is making your head dizzy. His office is perfumed nicely, smelling of him and the hundreds of ancient different books that are lined up around the room in towering bookshelves.

"But what about _Sabrina?_ " You can't help but gasp out, as he lifts your bottom and pulls down your panties and tights in one motion, leaving them pooled around your ankles. He shakes his head at you and chuckles again, staring you down incredulously while he undresses.

It's your favourite sound in the world — the sound of his belt buckle coming undone and then falling to the floor. He unzips his slacks and pulls his cock through the fly, so his pants stay on but his dick pokes up towards you. It's strangely erotic, and you lean back, pressing your knees together — exposing your sweet pussy to him. "Fuck," he says, and you shudder when he swears, " _what about her?_ Do you really think I was  _having some fun_ with her? All of my students are gorgeous, babe, but I don't just do _this_ with anyone." On the word _this,_ he opens your legs, and with an authoritative, firm thrust, he squeezes into your dripping pussy. "You must understand that. You are divine." He leans forward so you can wrap your arms around his neck, moving your body closer to his. "Part of my job is to occasionally touch other students when redirecting them, and I'm sorry of the fact. I understand it must be hard to watch. But we just need to—" his voice catches as you clench your vaginal walls, drawing his cock in deeper to you, "we need to communicate more. The start of any relationship always has ups and downs. Insecurity breeds jealousy. And not communicating breeds insecurity."

"Dean, with all due respect, you're being a total professor right now," you laugh, hoping to rile him up a little. You kiss him on the mouth, cupping his gorgeous face in your hands. He smells spicy — like cinnamon, and it sends warmth all around you. "But I totally get it. You're right, I was insecure. Can you fuck it outta me?"

"Oh, sweetheart, yes," he breathes. His thrusting fastens to an agonisingly pleasurable pace. "Sam misses you. _I_ missed you. Why don't you come home with me tonight? I wanna make it up to you…"

You can barely speak, so you just nod your affirmation, using your fingers to rub at your clit while he pushes into you. He's so thick, and grinding so perfectly — all you can do is gush out slick, pant, moan his name. His body heat rolls off him in waves, coating you and sending shivers through your bones. You are his. You are — utterly, and truly his. "I missed you both, too— I'm — shit! Really, really close—" you have to ease up your rubbing as you edge closer to that white-hot climax. "Dean—!"

His mouth rests on the crown of your head, his nose breathing in the scent of your floral shampoo. The sound of you fucking is obscene — just moans and skin hitting skin. "Baby, baby, baby, I'm gonna come," he repeats, a mantra he stains into your hair. "Where do you want it? Still on the pill?"

"Yes! Inside, please," you pant, thinking in your half-lucid state of the mess you'd rather not leave in his office, "p-please, Dean, I'm g-gonna come!" You can't keep your voice steady as you climax, your pussy rhythmically tugging at Dean's cock as you contract in pleasure. Feeling you shake under him is too much to bear, and his cock hardens in a final animalistic impulse, twitching with every spluttery, sticky contraction. You know he loves the feeling of his cockhead blurting out come, and you take every opportunity to revel in the moment with him. He's made up of shaky limbs and musky scent, and he's all but spent as he re-adjusts himself after pulling out of you. Sliding back on your tights, you're still half-naked, and you have to spend a good few minutes locating the rest of your variously-strewn articles of clothing. You walk like you're drunk. He laughs lazily in your direction.

"Your pussy," he groans, rubbing his face in the crook of his elbow, "is _fucking_ incredible. Babygirl, don't think I'm finished with you just yet — you haven't orgasmed enough in my honest opinion. But don't worry. When we get home, Daddy Dean and Uncle Sam are going to take care of you."

**Notes for the Chapter:**

> As always, leave something down below if this chapter... tickled your fancy, per se ;) You guys are absolutely the best and honestly I couldn't do it without you. Makes me feel a little bit more human, haha, to interact with y'all, and a little less like I'm throwing words into the void of the internet. If you've made it this far into the series, I wholeheartedly commend you, because this was never planned to be so long (and I can only see it getting longer from here!) and with so much warm reception. Love you guys and always remember you can be honest in the comments - I do appreciate not only little hellos but constructive criticism too, I know I've a ways to go in terms of quality of writing. My main goal is to be entertaining and erotic, so if I've got those down, I'll be pretty happy. Take care and happy holidays!


	16. Bigger Than Dad's

**Summary for the Chapter:**

> You feel Little.
> 
> WARNING: This chapter is focussed mainly around the ddlg (daddy dom/ little girl) kink, so please don’t read if you’re squicked out by that! I totally understand it’s not really everybody’s cup of tea, so I’m just leaving this warning here since it could potentially be triggering to some people.

**Notes for the Chapter:**

> I have no excuse for the obscenely long absence. I just hope you’ll accept this as a token of forgiveness ;D 
> 
> I may be absolutely shocking with sticking to a schedule, but you can’t say I don’t bring dat good shit. That I don’t PROVIDE dat sweet smut. Quality over quantity, babes! For those of you who have stuck around, thank you so so much! You deserve awards, all of ya.
> 
> By the way, this was getting long, so I split it into two parts.

Sam is gorgeous. Well, he always is, but in this moment — with the candlelight dancing around Dean and Sam's bedroom and throwing gold over his features — he’s heavenly. His smooth chocolate locks cascade down his face, framing his sharp jawline. He notices you staring and smiles, his dimples forming on either cheek as his lips curl sinfully. You want to kiss every inch of his face. And _those_ eyes of his, too, drive you wild; two smouldering, almost colour-changing orbs protected by dark and heavy lashes. A brooding look. It’s mesmerising.

"Are you gonna keep staring or are you gonna come over here and suck my cock?" He growls, his breath hitching as his eyes rake over your body. You can’t tell how serious he’s being. Your jaw clenches and you push a stray strand of hair behind your ear, but it comes loose again so you repeat the motion, using both hands to smooth it down. This is apparently amusing to him. "Nervous?"

The truth is, you can’t shake what Dean had said before you got here. _Daddy Dean and Uncle Sam will take care of you._ It sets fire to your body, makes your skin prickle with arousal. You’re hoping that Dean hasn’t forgotten. You don’t know how to bring it up again without dying of embarrassment. Dean fits the Daddy role well. _Wow_. You can’t even bring yourself to say the word out loud. It's so scandalous.  _Daddy._

Dean's watching you with catlike, squinted eyes, massaging his cock slowly as he spreads out on the bed. He strokes languidly, but you can see how excited he is. You wonder if he can read your thoughts. You’re gonna need some help if you want to articulate exactly what you want.

Speaking of Dean; he is picturesque. As always. His body is a paradisal landscape, comprised entirely of lean muscle and radiating heat all over. Everything about him — from his deep green eyes to his frustratingly pink mouth — is seductive. He just oozes sex appeal, and for a moment you forget where you are. Being with two naked men — two professors who might as well be carved from marble — tended to do that.

You almost forget to answer Sam. "A little," you breathe, and you bite your lip without thinking. Sam's eyes flicker down to your mouth for a second so fast you almost miss it. His chest heaves. _You know he wants you._ "You're just so— handsome. Both of you. I can't believe it. I'm so lucky."

Sam grins, one side of his mouth rising higher than the other. The poster boy for wickedness. "You're lucky? Jesus, we could say the same.” He drags out each word, his tongue wetting his lips. “You’re everything we could have asked for. Everything.”

Dean hums in agreement, his breathing stilted. You can feel how hard he’s trying to restrain himself from lunging at you. He’s practically buzzing. Finally, he saves you from yourself. “Do you want us to guide you, baby? You can let us do what we want with you. Or you can take control and order us around. It’s all up to you. Whatever you want.”

You want everything. “Um, I—” your eyes flicker between them. You’re in your underwear on their bed, facing them with your legs crossed. Usually, this type of hyper-focused attention would leave you feeling way too self-conscious to function, but there’s something about their combined presence that lifts your self-esteem. They make you feel wanted. They make you feel _sexy._ But there’s nothing forced about it, nothing contrived. It’s as easy as breathing for them. You look down at your legs that are covered in goosebumps and you smile. After gathering your voice, and mustering up all your courage, you say, “can we roleplay?”

Sam’s eyebrows jump up, but Dean doesn’t look surprised. Of course he doesn’t. “My little actress,” Dean says, and a smirk starts to stretch across his lips. “I would love to roleplay with you.” There’s a pause, and Dean looks over to his brother. “So long as that’s okay with you, Sammy.”

Sam’s grinning, cheeks flushed. “Well, I’m not the drama professor here, but I think I’ll be able to manage.” Sam puts a hand on Dean’s thigh, a small act of grounding himself. Sam’s hands are big and his fingers squeeze a little into Dean’s flesh. The image is erotic to you. “What type of roleplay?”

Dean’s picked up that you’re in a bit of a mood. You can’t even identify _what_ mood, but apparently, he can. “What did we talk about before we got here, huh?” Dean’s leaning closer to you, and his eyes are practically glued to your chest. Your heart is fluttering. “What were you excited about?”

Here goes nothing. _Do it_ , you think, _real quick like a band-aid_. “Daddy daughter,” you whisper, your voice barely audible. Your blush burns you. “With, with… Daddy Dean and… Uncle Sam.” Something’s happening to you. You don’t know exactly what. It’s getting harder to form coherent sentences, you feel like the room is expanding before your very eyes.

Sam laughs. “Uncle Sam? That’s cute. Fitting, because I do want you,” he thinks for a second. “But I dunno, it feels a little patriotic to me? How about I be your older brother, Y/N? Would that be all right with you?”

You nod feverishly; your eyes as wide as saucers. “I think she likes the sound of that,” Dean remarks to Sam, then turns back to you. “You like the sound of that, don’t you, babygirl?”

“Yeah,” you say, your voice coming out softer, higher-pitched than usual. Something is going on in your brain, something is making you feel doe-eyed and safe and small. Your body starts to curl in on itself — not in a scared or defensive way, but in a writhing, pleasurable way.

“Yes, what?” Dean asks, but his voice is deeper, his chin raised. You’re not quite sure what he’s asking from you until your voice cuts through the expectant silence and leaves your brain to catch up.

“Yes, daddy.” You peep. And then your hands fly up to cover your mouth! Your lips are pursed; you cover your face with your arms. You have no idea what’s happening to you. To your psyche. _Daddy_. As you think the word, a gush of wetness ruins your panties. The sweet, slightly musky smell of your arousal is permeating the room. Sam’s nostrils flare and he breathes in as deeply as he can. His cock bounces.

Sam squeezes Dean’s leg again. “Dean,” he says, and the faintest hint of concern flashes across his pretty face, “I think she’s going into little space.”

Dean’s nodding, observing you; you’ve got your knees up as you rest your chin on them, looking like the epitome of adorable. He concurs. “I think so too.”

“Has she done that before?” They’re whispering between each other, but you can hear them very clearly.

“I don’t know, but she seems to be enjoying herself.”

“And will I ever get my dick sucked?”

Dean grins but rolls his eyes. “Shut up, Sammy, we all know how much of a sucker you are for orgasm denial—” he pauses for a second. “No pun intended.”

You fill your cheeks with air and look between the two of them, a sweet smile on your face. “What’s little space?” You’re starting to slur your words. Your voice has more of a lilting, sing-song quality about it.

“Well…” Both boys start to speak. Dean lets Sam continue. “Well, it’s a… a headspace that good little girls like you go into when they feel comfortable, happy, and safe enough. Sometimes they go in and out of little space as they like. Some littles need a trigger, like a— a particular toy, or word or phrase that makes them feel protected and small.”

Your mouth makes an ‘o’ shape in understanding. “I feel small.”

“Yeah! Great. That’s great. And you're lucky, because have two strong, older men to guard you and make you feel good!” His voice is cooing, encouraging.

You like that. You love that. “I feel little,” you say again. “When you and Dean— D— _daddy_ talk to me like that. When you praise me.”

“C’mere, princess,” Dean says. You crawl over to him, across the bed, and squeeze yourself in between their big, warm bodies. You turn so you’re facing Dean more than Sam. Sam moves his hand from Dean’s leg to your back. “Do you wanna sit in daddy’s lap? You wanna bounce in daddy’s lap?” You nod your head. His voice is crooning, putting you further and further into a childish and subservient headspace. “Yeah? You do? Okay, well—” all of a sudden, his face falls dramatically. “Oh, no, you know what— I’m so sorry baby— but you can’t!”

He sounds genuinely upset.

“What! Why!” You pout. You’re upset, too.

“I’m sorry, baby. There’s something— in the way. There’s something in the way— that you’re not allowed to touch.”

 _Not allowed?_ Naturally, that piques your interest. Ever-curious, you decide to inquire further. “What is it?” Sam’s still rubbing your back, you feel his warmth seep into your skin. Looking down into Dean’s naked lap, your mouth starts to water. “What is that? It’s— it’s big.”

“You can’t— you weren’t mean to see that. That’s…” he sighs. He glances above you for a moment, at Sam. Waits for something. An affirmative maybe? “That’s daddy’s _cock._ ” His voice is beautiful and gravelly; you’re dripping. The way he says obscene words alone could make you come “That’s what some people have down there.”

“I don’t have one, daddy,” you say, your hands cupping the spot in between your legs. Dean laughs at the gesture. Sam starts to massage your shoulders.

“Well, that’s because you have something else there. You’ve got a pussy _._ Does that make sense? You have a _pussy_. Can you say that word?”

You’re equal parts aroused and embarrassed. But you want to be a good little, so you do as your daddy asks. “Pussy.”

Dean groans, his cock starting to drip. You can feel Sam’s erection poking into the back of your smooth, fleshy thigh. Sam’s trying his best, but he can’t help but rut up against you at times, especially when you wiggle your bottom against his torso. The sexual tension in the room is reaching a breaking point. “Oh, wow! Well done, baby.” Dean motions to where your hands are still cupped. “That’s your pussy. Some people have cocks, like me and your older brother, and some people have pussies, like you. Sometimes, a person might have a combination of the two — or maybe even something totally different down there. It really depends. But each person should be respected and made to feel safe.”

You lean back against Sam and his gorgeous touch. “My pussy feels funny.”

“Really? Does it feel all wet?” Sam whispers in your ear from behind you. “Does it feel like it wants to be touched?” Again, you feel his cock poking into your skin. Poor Sammy. You wonder how bad he wants it.

“Yes, it does, big brother.” You reply. Dean finally can’t help himself and starts to kiss all across your face — across your forehead, your eyelids, your cheeks — but he stops short at your lips, waiting for your permission. You nod gently and he places his lips on yours, savouring you. He tastes minty fresh. As you melt into the kiss, your hand wraps around his cock without thinking.

“Oh! God!” Dean exclaims. He’s taken aback, and Sam whines, observing and wanting the touch he’s not receiving. “What did I tell you? You’re — that’s daddy’s — you can’t touch that…”

"But I wanna make daddy feel good,” you mumble, your eyelashes heavy and downcast. Dean’s slowly losing all composure, even slipping out of the roleplay a bit. But you’re way too far into little space to come out anytime soon. “It looks like a really really big lollipop! Can I suck it? Please, daddy!”

Sam’s sexual energy could register on the Richter scale. “You’ve gotta be fuckin’ kiddin’ me,” he says, loudly, his hands moving down to grip and squeeze your waist, his groping careful and intentional but buzzing with impatience.

Dean smirks, and you’re ecstatic to hear what he says next. “Well… since you’ve been _such_ a good girl, I could probably let you… _just this once._ But don’t tell anybody! It’s between you and me.”

“And me,” chimes Sam, sounding faux-annoyed. “Hey little sis, how come you don’t want to suck my lollipop? Mine’s bigger than Dad’s!”

You giggle and use your free hand to grope around behind you, squeezing his stomach muscles and his pectorals. “I wanna lick yours too, but I can’t do both at the same time!”

“Yes, yes you can,” Sam says eagerly, “maybe not inside that cute little mouth of yours. But you can — you can lick them both at once. Dad? What do you think?”

“Whatever she wants,” Dean says, sternly, then looks towards you. “Whatever you want.” Dean might be the one ‘in charge’ in this scenario, but really, it all rests on your shoulders. _Whatever you want._ The words ring in your ears. Whatever you want.

It takes every shred of self-control you have not to shove your hand down your panties. “I want to lick you both, then.” You move away from them and gesture at the two brothers to move closer together. They seem to get the message, and face each other fully. They have to balance on their knees so they’re adequately close enough for their cocks to touch. Sam sucks in air through his teeth, his dick looking ready to burst. He’s rubbing against Dean, trying to get something, _anything._ You’re suddenly craving a mouthful.

“I’m so hard,” Sam whimpers, and for the first time you see him completely given over to you, _you,_ the supposedly small and naïve one in the situation. “Please lick me, little sis. Please lick us.”

“Be a good girl and use that talented tongue,” says Dean. And you do. You sit with your legs crossed again, and you move close enough that both their cocks touch your lips. They’re both so smooth, and pulsating with blood, and you waste no time opening your mouth to lick, suck, and toy with both of them. Sam looks and sounds like he’s going to cry with relief. You try to focus on them equally, so when you throat one of them you use your hands to stroke the other. No complaints from either of them. Only guttural, beautiful moans. Your panties have a growing dark spot on them. “Do you like sucking your daddy and your brother?” Dean asks. You moan your _yes_ , drooling all over both their cocks. Sam can’t help but buck into your hand, your mouth; he’s spurting pre-come like his life depends on it.

Their frottage is delicious. You put their two cocks together and use one hand to masturbate them both. You want them to feel each other. You want the friction to be tantalising, agonizing, absolutely _devastating_ in the best way _._ Sam’s making a mess all over Dean’s meat. You didn’t know he was so _drippy_.

“You know—” Sam starts, “my _girlfriend_ would kill me if she found out I was getting blown by my sister with my dad.” You’re confused for a second before you realise he’s adding to the roleplay. You giggle and take his cock into your mouth as deeply as you can.

After lathing him in attention for a few minutes, you pop his cock out of your mouth to gloat, your cheeks a deep scarlet. “Can your girlfriend do _that_?” You ask; not out of malice, but our of mischievousness. He shakes his head, _no, brat,_ and threads his long fingers through your hair, gripping you tightly to keep you in place as he stuffs your face with his cock again. Dean’s patient as he strokes himself off right against your cheek, his pre-come staining your skin.

When his knuckles meet your cheekbone on every upstroke, he makes sure to be gentle, almost giving you a caress. He can see that he and Sam are making a complete mess of you — and what’s more, that you love it. He tests the waters with what he can say as he continues to masturbate against your face. “You are, without a doubt, the prettiest little fucktoy I’ve ever had the pleasure of using,” he coos, and your jaw goes slack with his praise. It’s filthy, and so depraved, but it sends you into a type of animalistic lust — or at least, a little’s version of animalistic lust. Your eyes glaze over and roll into the back of your head, which just tells him to continue his smutty talk. “Daddy’s little princess. Daddy’s little whore. Daddy’s little cock sleeve.”

To hear you being called such naughty things almost sends Sam over the edge. “Fucking filthy… dad.” Sam looks down at you having the time of your life. You’ve pushed both their cocks together again but this time you’re using the flat of your tongue to lick both of their heads at once. “She’s gonna kill me with that mouth.” Pauses for a second. “You have a come kink, don’t you, baby sis?”

“Mhm!” You say, hyper-energetic, obsessed with the taste of them. You’re too focused to feel embarrassed.

Sam hums, and when you hit a particular sweet spot with your tongue, he shakes. “It’s your lucky day, then,” he replies, “’cause you’ve basically got come on tap.” As he says that, his cock starts to spurt again — not a full-blown orgasm, just pre-ejaculate — all over your hand and lips. The sight of that sets off Dean, and his cock dribbles a little bit too. You’re incredibly slimy and you wouldn’t have it any other way.

“Well yeah, with your excitable cock,” Dean chuckles, and he uses one of his hands to fondle Sam’s balls. “I’ve never seen a cock spurt as much as yours does. Your balls must be so full all the time. So heavy.”

“D-Dad, fuck, yeah…” Sam stutters, pleasantly startled by Dean’s sudden attention. "T-to be honest, I’m pretty cl-close right now so I think — we should start to focus on our l-little one…”

**Notes for the Chapter:**

> Watch out for part two! It's a doozy. And once again, thanks for sticking around. It doesn't need to be said but I'll say it anyway - to those of you still here, thank you so, so much! You inspire me to be better - a better writer, a better person, a better everything. Wishing you nothing but love and smut, smut, smut!


	17. Almost Pornographic, Really

**Summary for the Chapter:**

> Things go exactly how you hope, and then not at all.
> 
> CW: DDLG kink, panty-sniffing, semi-exhibitionism?

**Notes for the Chapter:**

> This fic is my favourite way to self-indulge… tell me, how do you like to self-indulge? Also: thoughts on more Cas? Or do you have your hands full between these two insatiable brothers?
> 
> I’ve got a couple ideas floating around about where to take this story. I really wanted to give this amazing community some interactivity, so I had this idea of the reader (Y/N!) having a deep and meaningful (or just light and playful) conversation with the Winchesters, where she finds out a bit about their backstory: how they came to be romantically involved, what their childhood was like, etc. If that’s something you guys might want, leave some questions in the comments for your beloved Professors! I’ll endeavour to have all of them answered in the next (or subsequent) chapters. Here’s to author-reader solidarity!

Dean agrees. “You’re right. She’s been so obedient. So good. She hasn’t even touched herself, though I can see the wet spot on her panties spreading with each suck.” He takes two of his fingers and shoves them in your mouth, silently expecting you to coat them in your saliva. He looks down at you. “Do you want us to teach you how to touch yourself?” You can only hum around his fingers. “Okay, well lie down—”

“—let me get this off of her first,” Sam says, unclasping your bra. Dean removes his fingers from your mouth. Your skin feels suddenly cold, so raw and exposed, and your little pink nipples catch the attention of both of them. Sam cups one of your breasts in his hands. “I’ve been dying to do that since we started. You have such sexy boobs, sis. I love watching your nipples get hard.”

“Take off her panties, too,” orders Dean, and you have to stand up on the bed — somewhat awkwardly — to give Sam access to roll down your panties to your ankles. His face is at your chest level as you do this, since he’s still balancing himself on his knees. You wonder if his muscles are hurting from keeping himself up for so long — you suppose the blowjob outweighs the discomfort. “Take your panties off,” Dean repeats, speaking to you this time; you balance on one foot each as you’re finally naked in front of them. Your pussy and thighs are immensely slick. They can see it when the light catches your skin — the glistening, tell-tale sign of total and utter arousal. Dean licks his lips. You note that he’s a very visual creature.

“Give them to me,” Sam says, and you comply, handing the damp cloth over. He puts the wet spot up to his face and breathes in as much as he can, making your jaw drop and your body go red all over. He holds onto them in a fist after that, choosing to keep your panties rather than discard them like he did with your bra. “Don’t judge. You smell — so fucking good.”

Dean’s amused, “she tastes good too. Didn’t I say that the first time all three of us were together?”

“You did, I remember,” Sam says, “I remember it specifically— because the way you sold it to me meant I had to have a taste. And now I’m hooked.” He forgets himself for a second, and then floats back into the world of fantasy. “I mean— this is totally the first time we’ve done anything like this, _dad!_ ” They both laugh, making you laugh, too. You’re surprised that you can still have moments like this — warm, intimate moments, even in the middle of sex, in the middle of _dirty_ sex, of _kinky_ sex — you’re surprised that there is still a lightness, still a fondness, still an ability to laugh and joke around and have fun. You’re suddenly overcome by a sweeping feeling of gratitude; it moves like a tidal wave over you and you have to actively focus on not bursting into tears. How on earth did you get so lucky?

“Y/N, lie down on your back.” As always, it’s like Dean can read your mind, because he gets you out of your head and back into the realm of pleasure and physicality. You do as instructed and the other two men follow suit, laying next to you on either side. You are completely surrounded by hot, chunky muscle and masculine scent. You could die happy here. The two of them face you in the middle. “Stroke us again.”

You’re glad that you’re somewhat co-ordinated with your non-dominant hand, because stroking two cocks in tandem isn’t as easy as it sounds. The moans start up again, but this time, Dean moves his hand down to your pussy, his fingers finding the clit that he loves to play with so much. Sam uses a hand to toy with your nipples, enjoying their reactivity, their playfulness. You can’t stop squirming.

“Big brother,” you whimper, and the honorific burns your tongue in the best kind of way, “why does that feel so good? It makes me feel sooo good.”

Sam laughs. “Well, sis, your boobs are really sensitive. Especially when you’re so _horny._ ”

“What does _horny_ mean?”

“Mmm…” Sam’s distracted, finding it hard to be coherent. “I think that’s a question for dad, hm, don’t you think?” His head lolls back as you continue to stroke him slowly, tightening and loosening your hand. The sounds pouring from his mouth are delicious. His hips can’t stay still, he’s squireling his cock in and out of your grasp, you barely have to move your hand. His whole body is damp with sweat— your eyes catch a clear bead of liquid moving down his Adam’s apple and you swallow nervously, still overwhelmed at the beauty, the _depravity_ of your interactions after all this time. 

It’s a task to take your eyes off Sam, but you manage to turn your head so you can lock eyes with Dean. His furrowed brow and bitten lip tell you that he’s close to coming. His cockhead is lush and red with blood, your hand glides smoothly over his shaft. He’s on the edge. You decide to play off that. “Daddy,” you whine, in your most adorable, most devious voice, “what does _horny_ mean?”

“Erm, well, baby—” words are not easy to produce, “—fuck, yeah, stroke me like that— _horny—_ is when— you feel, uh… sexually excited, baby. Oh god! Usually, y-you can stim— stimulate yourself to orgasm, or get… get someone else to do it for you.”

“What’s—oh!” Dean’s fingers are magic, you conclude, as he finds a perfect rhythm against your swollen clit. The squelching noise your pussy is making is obscene. Sam drapes your panties over his face. A hot flush courses through you. “Mmm! What’s _orgasm_ , daddy?”

“Keep stroking me like that, baby, and I’ll— I’ll show you.” His fingers on you are becoming more frantic, more searching. “When daddy and big brother orgasm, yummy liquid comes out _just for you_ , baby. Yummy yummy juice. You love juice, don’t you, b-baby?” His voice is so strained. You nod and whine, biting your lip. A gush of slick rushes out of your pussy at his words and he feels the sudden increase in wetness. It’s enough. “Oh, f-fuck, fuck, Y/N, Sammy, I’m gonna— I’m gonna— oh, _shit_ , yes, I’m coming!”

His cock spurts come violently, all over your stomach and chest, some of it even hitting Sam. You know Dean’s orgasm is more than enough to push Sam over the edge, so you move to take your hand off of Sam’s cock to keep him going just a _little_ longer. You’re stroking Dean through his orgasm, watching him shudder and his lower stomach tense and relax, watching stream after stream of come hit your skin. There’s so much. It’s all over you, and so warm, _so warm._ Throughout his whole convulsing orgasm, Dean hasn’t stopped rubbing you off, and you’re quickly reaching your peak. All you can hear are the ragged, broken sounds coming from Dean and the frantic panting coming from Sam.

“Fuck, I’m coming, I’m coming, I’m coming, oh, fuck, fuck, uhn—” Sam’s grunting is unashamedly loud, and you’re amazed as you watch his cock orgasm without being touched. If you were covered in come before, you’re absolutely _drenched_ now, white streaking your skin and dribbling down your sides, mixing with the sweat of the two men you’re sandwiched between. “Touch me, touch me, touch me, please, stroke me—” his voice is muffled by your panties over his face, but you quickly get the message, stroking him through the rest of his orgasm, making his entire body jerk and shake, his back arching off the bed. It feels like hours before his body hits the bed again; figuratively and literally coming down from a huge high. You don’t know what to make of the mess that has transpired in ribbons across your body.

“God, Sammy, you shot off without even being touched?” Dean’s impressed, his voice a murmur, a bassy undercurrent to the buzzing in the room. His fingers bring you close a number of times, getting you right where you need to be, before moving off you for a split second. You know what he’s doing but you love it. Your body feels like it’s no longer yours, and you have no energy or control whatsoever, so you lay there in spiralling bliss and let Dean bring you off with his talented fingers. “Nice, bro.”

Their post-orgasm talk is bringing you slowly out of little space, but you don’t mind. “I’m hungry,” Sam says, finally removing your panties from his face and gently placing them on the bedside table. He grabs a small towel from the drawer to clean himself of any miscellaneous fluids. “Is it okay if I get something to eat?”

You would turn your head to look at him, but you’re so invested in your impending orgasm that you can’t see anything, just a hazy fog that blurs your vision. Dean shrugs beside you and _just_ catches the towel that Sam throws at him. He cleans himself off but leaves you covered in come. “Sure,” he says. When you make a pouting face at him for not cleaning you up too, he says, “what’s wrong, baby? Don’t you like being covered in come like the little slut you are?”

It’s a power move. Your eyebrows jump for a second and you bite your lip. It isn’t your _daddy_ saying it this time, it’s _Dean_ , and _somehow_ , for some reason, it feels different. Almost dirtier, though it seems oxymoronic, almost more personal. There is no façade. Purely just you and your professor calling you filthy things as he brings you again and again to the edge of orgasm. Sam moves towards the other end of the bed. You stutter for a moment, your head spinning, before you’re able to coax out some words.

“S-Sam… what are you—” he’s kissing your feet, moving up your legs to your calves. You want to stay here forever. You thank God it’s the start of the weekend. “Ooh, that feels so fucking—”

_Ring! Ring! Ring!_

You’re interrupted by the familiar sound of your ringtone pulsating through the air. You jump, startled by the sudden infiltrator in the room, and you look at Dean like he’s grown a second head when he hands your phone to you. “Answer it,” he says, and he looks more authoritative than you’ve ever seen him before.

“Are you crazy?” You reply, your face twisting in confusion and then pleasure as the pads of his fingers swirl your clit. You’re swinging like a pendulum between those two emotions, unsure of where to land or how to feel. He just continues to look at you with an expression of pure dominance and expectancy, almost bordering on impatience. The more you just look back at him, the slower his movements get, until his fingers are teasing, _just_ resting on your pussy. You know you can’t win this battle. You huff and take your phone from his hand, trying not to make it too sticky with the saliva and come that your hands are coated in. You don’t bother to look at the caller ID before answering. “U-um…” you try and sound like you’re not in the middle of a sweaty, steamy sex-session. “Hello?”

“Hey. Y/N? Is that you?” All at once, your body seizes up, and you try to squirm away from Dean’s touch. The bastard has resumed his ministrations against your clit, and you know that you’re not going to be able to maintain any type of decency. “You sound… different.”

“Castiel,” you breathe, and Dean’s fingers get faster — you’re not sure if it’s out of jealousy or cheekiness. “Um! Yeah, it’s me. What’s up— what did you, did you need something?” Your voice is husky, low, you’re sure you sound lewd and as Castiel put, _different._ Sam’s snickering from where he’s poised, moving his kisses up to your knees and then your thighs and you want to all but _scream_ but you can’t—

“Yes, actually, I wanted to know if you were…” he pauses when you sigh involuntarily as Sam sucks kisses _so close_ to your pussy. “If you were… free… sometime. To meditate. With me.”

You’re frowning, trying to remember _when the hell_ you ever mentioned you were into meditation. Then it hits you. “Oh! Oh… yeah…” your voice sounds filthier than it should. “I did… say that’s what I’ve been doing r-recently.”

Castiel, you hope, is oblivious. “And you’ve just been, I suppose, so  _happy_ recently, I wanted to try it out… with you. Maybe find some stress-relief. The Lord knows I need it.”

Dean’s fingers stop moving all of a sudden, and you’re about to make a questioning motion when Sam’s soft lips latch onto your sensitive pussy. “Fuck!” You exclaim, clamping a hand around your mouth, your cheeks staining with embarrassment. Sam’s tongue and lips get to work straight away, and you bring the phone away from your face for a moment to quietly hiss, “what _are you doing_?!”

He whispers back to you, infinitely wicked, “I told you, getting something to eat!” The sounds of his tongue lapping at your pussy are so filthy, you could die. It’s squelching and kissing and it’s bringing you closer and closer to orgasm and you have no idea what to do.

You hear Castiel’s muffled voice coming through the speakers so you have no time to argue with Sam. You bring your phone back to your ear, “—sounds like you’re with someone or something, are you with someone, Y/N?”

There’s no way you could ever explain just what kind of predicament you’re in. “Um! No. I’m by my— alone. Home alone, that’s me, I’m alone. At my house. It’s the… TV. I’m watching TV.”

“What’s that slurping noise?” He asks, innocence incarnate, and your face goes even redder. Dean’s close enough to just make out what Castiel is saying, and his jealousy morphs into hilarity as he has to shove his face into a pillow to stop himself from cackling out loud. His body shakes next to you from his silent laughter and you have to scramble to think of a decent response.

“I’m, ah…” you look down at Sam. “Eating. Oh, it’s so good…” you can’t hold in your moans anymore, Sam’s tongue is just something else.

“Sounds delicious,” he replies, and his voice is painfully sincere. “Sounds like I need some of that."

“Huh?” You ask, your hand starting to shake, your body seconds away from orgasm.

“Maybe I can have some of what you’re having one day? Next time I see you? It sounds amazing. Like, whatever you’re—” you have to pull the phone away from your ear for a second, to motion to Sam that you’re _about to come_ , “—sounds divine, almost pornographic really, Y/N, those noises—”

You can’t help yourself. You come. You come, you come, you come, _hard_. And it wrecks you, it shoots throughout your whole body; you drop the phone as both your hands cover your mouth to stop you from shouting, from yelling, from spilling forth hundreds of obscenities as your vision fades completely and Sam licks you through the most intense orgasm you’ve ever had.

 _Sam Sam Sam!_ You don’t know if you’re screaming his name out loud or not, it just echoes around in your head and it’s the only thing you can think about. Your thighs squeeze his head even closer to you; he smiles as he drinks out as much ecstasy as he can from you. Your body is fraught with trembles, a shiver continues to roll through you even after you stop twitching. You’re almost, _almost_ too blissed out to realise that Cas is still on the phone.

Dean holds your phone up to your ear since you can’t move a muscle. Sam’s wiping down your sweat-and-come-drenched body with a towel. You’re still twitching.  “Um…” you have no idea what to say. Your brain isn’t working, the synapses not firing. A heavy sleep is threatening to pull you in — your vision still unclear and lazy. “S-so. Cas. Castiel.” Are you slurring your words? You’re slurring your words. Sam stops wiping you down and throws the towel on the ground, jumping up to get dressed. You still can’t move. “Castiel.”

“Stop— stop… saying my name.” The tone of his voice hurts you, you can’t think of anything else to say. You suppose he can’t either. The silence on the other end of the line is deafening. You hold your breath. Dean puts the phone on speaker so he can gently place your phone next to your face on the pillow and _he_ can put a shirt on. “So. Uh… I— I don’t know exactly what— what’s going on with you… I don’t know what _that_ was, but I— I think that we need to talk, Y/N. You’ve been distant and cold and then warm and then happy-go-lucky and you’re suddenly keeping secrets and hiding from me? When did this happen— to _us_ , t-to our friendship?” Your eyebrows crinkle but you can’t refute any of what he says.

“I’m so, so, sorry—” his name is on your lips but you think against it, “things have been _so_ crazy and I wish I could tell you what’s been going on—” Dean gives you a stern look as he finds a clean pair of underwear to put on, and he smacks Sam’s ass on the way to the drawer. “I wish I wasn’t such a terrible friend… I’m sorry. If you wanna talk, let’s talk. Let’s talk now.” Your tongue is thick in your mouth, pushing your words out strangely. Your breathing is _just_ returning to normal.

“Exactly what I was thinking. I’m driving to your place right now.”

Your heart all but stops. “Wh-what do you mean? I’m not there.”

Castiel is frustrated, you hear him sigh into the phone. “You _just said_ you were watching TV at your place.” You’re being backed into a corner and you don’t know what to do.

You find enough energy to sit up on the bed, ignoring the head rush that follows. You’re looking between Dean and Sam frantically as they meander about half-naked. You’re trying to find _some_ type of guidance, any bit of advice that might help in a situation like this. They both just look at you blankly, as if to say, _well, you’re on your own, kid._

“I did. I did say that. I did just say that.”

“Look, Y/N, I’m about five minutes from your place so I’ll talk to you when I get there—”

You don’t know what’s worse: lying to your best friend _again_ to avoid him finding out you lied the first time, or letting him go to your house and find out you’re not there. The seconds tick by too fast for your liking. “No! Castiel, I’m so sorry, but you can’t come in because I’m with a— I have a new— I’m with a boy and it’s meant to be a secret!” You get a squinted, warning look from Dean,  and you quickly have to cover your tracks. “I met him in my drama class, he’s tall, and really handsome, and my parents would totally disapprove, and that’s why I’ve been so secretive lately, I’m sorry, Cas. But you really can’t come over right now, because we’re not ready to go public yet. We're just not comfortable with that right now. I really hope you understand.”

Castiel doesn’t say anything, and you wish you could see his face to read his expression. “Okay,” his voice cracks, and you’re slightly shocked that he believes it, “sorry for caring, I guess.” He sounds bitter, and you’re not sure if it’s about the lying or something else. “Turning back home now.”

You breathe out a sigh of relief, but you're devastated that your highest high is so quickly crashing into your lowest low. “Thanks, Cas,” you say. “Thank you, really. For being the best friend to a really shitty friend.”

“Don’t—” he says again, and you find your lip quivering. Your arms wrap around your torso and your toes curl unpleasantly. “Just— just tell me one thing. Tell me, Y/N, if you _so want_ to be a good friend like you keep saying. If you _really do_ feel so sorry about your lying and deceit and dismissiveness. Tell me, so I can believe you, so I can regain some type of trust in you, tell me, _tell me what his name is._ ”

 _Names_ would be more appropriate, you think, but you know you can’t implicate either Winchester by bringing up their names, and _especially_ not Dean. Both he and Sam are looking at you and shaking their heads, making it very clear that neither of them want their name tossed into the ring. You don’t know what to say. 

You think about the only other people you know who might be interested in helping you out. You need a boyfriend. Well, a pretend one — you have enough real ones. You’re very aware of the growing impatience on the other end of the line. “Um… his name…”

You’re starting to sweat when it hits you. _Andy. Luca. Kristian_. You’re fairly sure your fellow actors would be glad to help you out, or at the very least be interested in getting more improv training in. You ignore your moral compass and succumb to lying again, and you make the mental note to call one of the boys as soon as you’re off the phone with Castiel. But you have to choose one now — Castiel won’t rest until he’s gotten a name from you and you just hope you’re about to make the right decision.

 _Andy_. The handsome, blonde-haired, green-eyed footballer that dazzles everyone he meets.

 _Luca_. The studious, artsy boy with the messy brown hair, cheeky smile and rich, contemplative voice.

 _Kristian_. The grey-eyed, stoic, and well-read type with dark stubble and dark freckles, and an oozing sensuality that you can feel across a room.

Choices and names, choices and names.

“I’m waiting…” Castiel is perturbed.

“His name is—”

**Notes for the Chapter:**

> Interactivity! Pick your favourite out of those three handsome men. The one with the most votes will be featured in your future antics.
> 
> Thank you guys so much for your time! I'm also currently looking for a beta reader. Lemme know if that’s something you’d be interested in! Also, how would you feel about making one-shot requests that I could write and post in between (or alongside) updating this story? As seperate works, of course, but I was just wondering if people would want that? Too many ideas, too little time!
> 
> Lastly! Would anyone be interested in my tumblr?


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